Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.

This journal is © The Royal Society of Chemistry 2022

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.

This journal is © The Royal Society of Chemistry 2022

Supporting Information for...

CBr4 Catalyzed Activation of α,β-Unsaturated Ketones

Shyamal Kanti Bera,a Rajat Rajiv Maharana,b Kousik Samanta*,b and Prasenjit Mal*,a

a
School of Chemical Sciences, National Institute of Science Education and Research (NISER),

An OCC of Homi Bhabha National Institute, Bhubaneswar, PO Bhimpur-Padanpur, Via Jatni,

District Khurda, Odisha 752050, India

b
School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Argul, Odisha

752050, India

CONTENTS

General methods and experimental procedure S2-S5

Crystallographic data S5-S12

Computational Details S12-S78

Characterization data S78-S101

References S102-S103

NMR Spectra S104-S239

S1
EXPERIMENTAL SECTION

General Information. Commercially available reagents and solvents were used as received.

Column chromatographic purifications of the compounds were performed using silica gel

(mesh 230–400, 100-200) and hexane – ethyl acetate solvent mixtures. NMR spectra were

recorded on a 400 MHz or 700 MHz instrument at 25 °C. The chemical shift values are reported

in parts per million (ppm) with respect to residual trichloromethane (7.26 ppm for 1H and 77.16

ppm for 13C). The peak patterns are designated as follows: s: singlet; d: doublet; t: triplet; q:

quartet; m: multiplet; dd: doublet of doublets; td: triplet of doublets; brs: broad singlet. The

coupling constants (J) are reported in hertz (Hz). High-resolution mass spectra (HR-MS) were

recorded on an ESI-TOF (time of flight) mass spectrometer. Infrared spectral data are reported

in wave number (cm-1). FT-IR spectra were recorded after making thin layer of the compounds

on the surface of NaCl crystal using dichloromethane. Melting points of the compounds were

determined using a digital melting point apparatus and are uncorrected.

General Procedure for the Preparation of 2ʹ-amino or 2ʹ-hydroxy Chalcones.1

2-Amino and 2-hydroxy chalcone derivatives were synthesized with the help of advanced

literature procedure.1 A round bottom flask containing a magnetic stirring bar was charged with

acetophenone derivatives (1 equiv) in ethanol and 50% w/v NaOH (5 mL). Then mixture was

kept in 0 oC and corresponding benzaldehyde (1.1 equiv) was added. Then reaction mixture

was stirred for 12 h and organic layer was separated by using ethyl acetate. Crude reaction

mixture was purified by column chromatography to afford the chalcone derivative as a yellow

solid.

S2
Representative Procedure for Synthesis of 2-phenylchroman-4-one

A sealed tube equipped with (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1a) (0.44

mmol, 100 mg) and CBr4 (30 mg, 0.08 mmol) was taken 2 mL ethanol. Then the reaction

mixture was placed in preheated oil bath (80 oC) for 12 h and reaction was monitored by TLC.

After completion of reaction, the crude residue was dried over vacuum and purified by column

chromatography to produces the cyclized products.

Preparation of 1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one (5a).2

Phenylacetylene (621 µl, 5.65 mmol) was taken in a 15mL dry THF solvent, and then n-butyl

lithium (5.65 mmol, 2.3 equiv) was added dropwise at -78 oC under Ar atmosphere. The

solution was stirred for 1 h at the same temperature. Then the 2-hydroxybenzaldehyde (2.45

mmol, 1 equiv) was added dropwise with continuous stirring at -78 oC under Ar atmosphere.

The reaction mixture was allowed to stirrer for 2 h at -78 oC and followed by 30 min at 0 oC.

Upon completion of the reactions, the reaction mixture was quenched with saturated aqueous

NH4Cl at 0 °C. The organic layer was extracted with 30 mL (2×15 mL) ethyl acetate and dried

over anhydrous Na2SO4, and the resulting solution was evaporated to dryness. The crude

product was purified by silica gel column chromatography with n-Hexane-EtOAc, to afford the

product 2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol with 69% yield. Then this product was

used for the next step.

S3
In an oven-dried round-bottom flask compound 2-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol

(360 mg, 1.6 mmol, 1.0 equiv) was dissolved in acetone (10 mL) at room temperature and

MnO2 (699 mg, 8.03 mmol, 5 equiv) were added on the reaction vessel. The reaction mixture

was stirred for 12h at the same temperature. Upon completion of the reactions (TLC showed

complete consumption of starting material), the reaction mixture was filtered using Buckner

funnel and washed with Dichloromethane. The filtrate was concentrated in vacuo, and the crude

product was purified by flash column chromatography with n-Hexane- EtOAc to obtain the 1-

(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one (5a) with 82% yield.

Preparation of 2-phenyl-4H-chromen-4-one (5b)

In an oven-dried sealed tube, 1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one (5a) (0.36 mmol,

80 mg) and CBr4 (24 mg, 0.07 mmol) was taken 2 mL ethanol. Then the reaction mixture was

placed in a preheated oil bath (80 oC) for 12h and the reaction was monitored by TLC. After

completion of the reaction, the crude residue was dried over vacuum and purified by column

chromatography to produce 2-phenyl-4H-chromen-4-one (5b) with 73% yield.

Preparation of 2-(4-isopropylphenyl)chroman-4-ol (6a).3

S4
In an oven-dried round bottom flask, sodium borohydride (0.375 mmol, 14 mg) in methanol

was charged with a stirred solution of 2-(4-isopropylphenyl)chroman-4-one (2f) (100 mg,

0.375 mmol) at 0 oC. Then the reaction mixture was stirred at room temperature, typically ̴ 2h.

The progress of the reaction was monitored by thin-layer chromatography (TLC) using ethyl

acetate and hexane as eluent. After completion of the reaction, the mixture was concentrated

under a vacuum. The crude residue was quenched with 15 ml saturated solution of NaHCO3

and ethyl acetate was added to extract the organic layer. Then the organic layer was dried over

anhydrous Na2SO4 and the resulting solution was evaporated to dryness. The crude product

was purified by silica gel column chromatography with n-Hexane-EtOAc, to afford the product

2-(4-isopropylphenyl)chroman-4-ol (6a) with 94% yield.

X-ray crystallography analysis

Crystal measurement:

The crystals data were collected with Bruker SMART D8 goniometer equipped with an APEX

CCD detector and with an INCOATEC micro source (Cu-Kα radiation, λ = 0.71073 Å).

SAINT+4 and SADABS5 were used to integrate the intensities and to correct the absorption

respectively The structure was resolved by direct methods and refined on F2 with SHELXL-

97.6 ORTEP drawing of the compound 2d, 2k, 4f and 4g shows ellipsoid contour at the 50%

probability level.

X-ray crystallography analysis

Procedure for preparing the crystal sample. In a 10 mL round bottom flask 20 mg of

flavonoids and aza-flavanone derivatives (2d, 2k, 4f and 4g) was dissolved by using ethyl

acetate and hexane mixture = 1:1 (6 mL). After that the solution was allowed for slow

evaporation to obtain good quality of crystal.

S5
Crystallographic data

Figure S1. Crystal structure of 2d (50% ellipsoid probability).

Table S1. Crystal data and structure refinement for 2d.

CCDC No 2100736

Empirical formula C15H11O2Cl

Formula weight 258.69

Temperature/K 100.00(10)

Crystal system monoclinic

Space group P21/n

a/Å 11.86690(10)

b/Å 5.12440(10)

c/Å 19.6290(2)

α/° 90

β/° 92.6480(10)

γ/° 90

Volume/Å3 1192.38(3)

Z 4

ρcalcg/cm3 1.441

μ/mm-1 2.752

S6
F(000) 536.0

Crystal size/mm3 0.2 × 0.18 × 0.18

Radiation CuKα (λ = 1.54184)

2Θ range for data collection/° 8.536 to 150.594

Index ranges -14 ≤ h ≤ 12, -6 ≤ k ≤ 6, -24 ≤ l ≤ 24

Reflections collected 16935

Independent reflections 2447 [Rint = 0.0276, Rsigma = 0.0118]

Data/restraints/parameters 2447/0/163

Goodness-of-fit on F2 1.073

Final R indexes [I>=2σ (I)] R1 = 0.0315, wR2 = 0.0819

Final R indexes [all data] R1 = 0.0317, wR2 = 0.0820

Largest diff. peak/hole / e Å-3 0.30/-0.34

Figure S2. Crystal structure of 2k (50% ellipsoid probability).

Table S2. Crystal data and structure refinement for 2k.

CCDC No. 2100734

Empirical formula C19H14O2

Formula weight 274.30

Temperature/K 293(2)

Crystal system monoclinic

S7
Space group P21/n

a/Å 16.01478(16)

b/Å 4.81292(5)

c/Å 18.38696(17)

α/° 90

β/° 94.4467(9)

γ/° 90

Volume/Å3 1412.96(2)

Z 4

ρcalcg/cm3 1.289

μ/mm-1 0.658

F(000) 576.0

Crystal size/mm3 0.2 × 0.2 × 0.18

Radiation CuKα (λ = 1.54184)

2Θ range for data collection/° 7.054 to 150.57

Index ranges -20 ≤ h ≤ 17, -6 ≤ k ≤ 5, -22 ≤ l ≤ 18

Reflections collected 23012

Independent reflections 2873 [Rint = 0.0291, Rsigma = 0.0172]

Data/restraints/parameters 2873/0/190

Goodness-of-fit on F2 1.035

Final R indexes [I>=2σ (I)] R1 = 0.0384, wR2 = 0.1082

Final R indexes [all data] R1 = 0.0407, wR2 = 0.1105

Largest diff. peak/hole / e Å-3 0.12/-0.16

S8
 Figure S3. Crystal structure of 4f (50% ellipsoid probability).

Table S3. Crystal data and structure refinement for 4f.

CCDC No 2100735

Empirical formula C15H12NOCl

Formula weight 257.71

Temperature/K 100.00(10)

Crystal system monoclinic

Space group C2/c

a/Å 17.5707(3)

b/Å 10.71140(10)

c/Å 13.5943(2)

α/° 90

β/° 105.535(2)

γ/° 90

Volume/Å3 2465.07(6)

Z 8

ρcalcg/cm3 1.389

μ/mm-1 2.620

F(000) 1072.0

S9
Crystal size/mm3 0.2 × 0.18 × 0.18

Radiation CuKα (λ = 1.54184)

2Θ range for data collection/° 9.772 to 150.748

Index ranges -22 ≤ h ≤ 21, -13 ≤ k ≤ 12, -17 ≤ l ≤ 16

Reflections collected 18437

Independent reflections 2519 [Rint = 0.0422, Rsigma = 0.0179]

Data/restraints/parameters 2519/0/163

Goodness-of-fit on F2 1.028

Final R indexes [I>=2σ (I)] R1 = 0.0481, wR2 = 0.1238

Final R indexes [all data] R1 = 0.0487, wR2 = 0.1242

Largest diff. peak/hole / e Å-3 1.28/-0.66

Figure S4. Crystal structure of 4g (50% ellipsoid probability).

Table S4. Crystal data and structure refinement for 4g.

CCDC No 2100733

Empirical formula C15H12N2O3

Formula weight 268.27

Temperature/K 293(2)

S10
Crystal system triclinic

Space group P-1

a/Å 7.5622(4)

b/Å 8.5111(5)

c/Å 10.0206(5)

α/° 88.894(4)

β/° 75.135(4)

γ/° 85.294(4)

Volume/Å3 621.27(6)

Z 2

ρcalcg/cm3 1.434

μ/mm-1 0.842

F(000) 280.0

Crystal size/mm3 0.2 × 0.18 × 0.18

Radiation CuKα (λ = 1.54184)

2Θ range for data collection/° 9.13 to 150.464

Index ranges -9 ≤ h ≤ 9, -9 ≤ k ≤ 10, -12 ≤ l ≤ 12

Reflections collected 10647

Independent reflections 2514 [Rint = 0.0425, Rsigma = 0.0279]

Data/restraints/parameters 2514/0/181

Goodness-of-fit on F2 1.090

Final R indexes [I>=2σ (I)] R1 = 0.0667, wR2 = 0.1827

S11
Final R indexes [all data] R1 = 0.0711, wR2 = 0.1866

Largest diff. peak/hole / e Å-3 0.99/-0.52

Computational Results

The quantum chemical calculations were performed using Gaussian 16 software7 at a High

Performance Computing Environment (HPCE) provided by NISER Bhubaneswar, INDIA. The

geometry optimizations were done without symmetry constrains using Density Functional

Theory at the level of M06-2X/6-311+G(d,p). The electrostatic potential of 2ʹ-aminochalcone

and 2ʹ-hydroxychalcone with tetrabromomethane (CBr4) were mapped on the 0.0004 au

isodensity surface with GaussView 5.

1. Optimized geometry and the energies of 2-Aimno chalcone at M06-2X/6-311+G(d,p)

Level

 SCF energy: -709.2751876 Hartree

 Zero-point correction: 0.243024 (Hartree/Particle)

 Thermal correction to Energy: 0.257380 Hartree

 Thermal correction to Enthalpy: 0.258324 Hartree

S12
  Thermal correction to Gibbs Free Energy: 0.200177 Hartree

 Sum of electronic and zero-point Energies: -709.032155 Hartree

 Sum of electronic and thermal Energies: -709.017799 Hartree

 Sum of electronic and thermal Enthalpies: -709.016855 Hartree

 Sum of electronic and thermal Free Energies: -709.075002 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C 3.11347700 -1.69717000 0.44990100

C 2.13810900 -0.72913800 0.73231100

C 2.16149700 0.47602200 0.00597000

C 3.16685300 0.68637700 -0.94338100

C 4.11821100 -0.27971500 -1.22202400

C 4.08237700 -1.47972000 -0.51357500

H 3.09966000 -2.62822800 1.00682700

H 3.18138000 1.64045800 -1.45758300

H 4.87997500 -0.10204900 -1.97018700

H 4.82021800 -2.24979600 -0.70722700

C 1.21582200 1.62371300 0.23072100

O 1.64637700 2.75619100 0.30700700

C -0.24799700 1.39679000 0.29255400

H -0.81286900 2.24886500 0.65724800

C -0.83805100 0.28102100 -0.15425700

H -0.20531800 -0.52838600 -0.51083900

C -2.27991600 0.01050700 -0.19351900

S13
C -3.24513400 1.00707200 -0.00047300

C -2.70583500 -1.30122200 -0.42567400

C -4.59538600 0.69194600 -0.02335400

H -2.93802000 2.03479200 0.15297100

C -4.05875700 -1.61804500 -0.44516200

H -1.96305800 -2.07642400 -0.58159600

C -5.00679100 -0.62168000 -0.24209900

H -5.33266200 1.47237000 0.12312800

H -4.37197900 -2.64007200 -0.62148800

H -6.06295000 -0.86313100 -0.26069400

N 1.18097000 -1.01840500 1.70369900

H 0.67116500 -0.23866400 2.08976300

H 1.48578300 -1.67096300 2.41009000

2. Optimized geometry and the energies of Aza-flavanone at M06-2X/6-311+G(d,p) Level

 SCF energy: -709.304661441 Hartree

 Zero-point correction: 0.245804 (Hartree/Particle)

 Thermal correction to Energy: 0.258824 Hartree

 Thermal correction to Enthalpy: 0.259769 Hartree

S14
  Thermal correction to Gibbs Free Energy: 0.204394 Hartree

 Sum of electronic and zero-point Energies: -709.058857 Hartree

 Sum of electronic and thermal Energies: -709.045837 Hartree

 Sum of electronic and thermal Enthalpies: -709.044893 Hartree

 Sum of electronic and thermal Free Energies: -709.100267 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C -2.41455324 -1.92801795 0.19047059

C -1.59738544 -0.79366989 0.06320065

C -2.20561965 0.46973668 -0.05163840

C -3.60003996 0.57878633 -0.03000173

C -4.39821388 -0.54137565 0.09889975

C -3.79061620 -1.79756339 0.20575375

H -1.95491865 -2.90668602 0.27953771

H -4.02602599 1.57112319 -0.12562805

H -5.47675317 -0.45229743 0.11358354

H -4.40370610 -2.68607558 0.30599024

C -1.37523168 1.68263199 -0.25390931

O -1.84643175 2.79435748 -0.32613810

S15
C 0.11250237 1.43455509 -0.41712296

H 0.65741566 2.34066817 -0.15099086

C 0.57927145 0.23937421 0.41584301

H 0.40586537 0.47505002 1.47788869

C 2.05309271 -0.02974076 0.21744714

C 2.97886732 0.43242829 1.15070351

C 2.50884935 -0.69571633 -0.92115037

C 4.34198542 0.23956455 0.94930671

H 2.63034875 0.94637419 2.04093063

C 3.87035804 -0.89405211 -1.12014406

H 1.78942504 -1.05982149 -1.64662622

C 4.79033310 -0.42513713 -0.18657857

H 5.05204684 0.60467723 1.68198960

H 4.21422721 -1.41426255 -2.00647553

H 5.85114676 -0.57995089 -0.34351149

N -0.21672487 -0.92104082 0.02758896

H 0.29950982 1.21936699 -1.47645125

H 0.12834824 -1.79656353 0.39926678

S16
3. Optimized geometry and the energies of Transition State (TS) of azaflavanone

formation at M06-2X/6-311+G(d,p) Level

 SCF energy: -709.206197275 Hartree

 Zero-point correction: 0.240728 (Hartree/Particle)

 Thermal correction to Energy: 0.253338 Hartree

 Thermal correction to Enthalpy: 0.254282 Hartree

 Thermal correction to Gibbs Free Energy: 0.199338 Hartree

 Sum of electronic and zero-point Energies: -708.965554 Hartree

 Sum of electronic and thermal Energies: -708.952944 Hartree

 Sum of electronic and thermal Enthalpies: -708.952000 Hartree

 Sum of electronic and thermal Free Energies: -709.006944 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C 2.27590900 -1.90198800 0.53948800

C 1.58116200 -0.71317000 0.36338900

S17
C 2.20435800 0.45227800 -0.08288400

C 3.56378500 0.40645800 -0.37850100

C 4.27109100 -0.77989100 -0.23508600

C 3.63004700 -1.92955700 0.22691600

H 1.77006100 -2.79034800 0.90181400

H 4.03914700 1.32457800 -0.70413600

H 5.32737400 -0.81392700 -0.47271900

H 4.18566100 -2.85214100 0.34292200

C 1.41571400 1.74389800 -0.14790700

O 2.01696100 2.80675200 -0.24088600

C -0.00720800 1.57017100 0.00681600

H -0.61664600 2.44855600 -0.17609100

C -0.54778000 0.21294200 -0.39974900

H -0.22164600 -0.17544000 -1.37136900

C -2.03241800 0.01789600 -0.23546000

C -2.73854400 0.64703300 0.79224300

C -2.71205900 -0.83856700 -1.10209600

C -4.10033900 0.41557500 0.94933700

H -2.22024900 1.32916100 1.45660100

C -4.07586400 -1.06501900 -0.94881700

S18
H -2.17052100 -1.32165200 -1.90892600

C -4.77142100 -0.43944700 0.07998400

H -4.64074200 0.91106500 1.74704800

H -4.59407700 -1.72462200 -1.63448200

H -5.83426000 -0.61191400 0.20045100

N 0.18178100 -0.57677900 0.67923100

H 0.09501500 0.50776200 1.23580600

H -0.26588200 -1.43931900 0.98952900

4. Optimized geometry and the energies of Carbon tetra bromide (CBr4) at M06-2X/6-

311+G(d,p) Level

 SCF energy: -10334.7423461 Hartree

 Zero-point correction: 0.007303 (Hartree/Particle)

 Thermal correction to Energy: 0.013994 Hartree

 Thermal correction to Enthalpy: 0.014938 Hartree

 Thermal correction to Gibbs Free Energy: -0.027665 Hartree

 Sum of electronic and zero-point Energies: -10334.735043 Hartree

S19
  Sum of electronic and thermal Energies: -10334.728353 Hartree

 Sum of electronic and thermal Enthalpies: -10334.727408 Hartree

 Sum of electronic and thermal Free Energies: -10334.770011 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C 0.00030506 -0.00006877 -0.00069828

Br 1.01976710 1.62322642 0.31983062

Br 1.21217906 -1.44193226 -0.47807490

Br -1.25658010 0.29968142 -1.45052041

Br -0.97541836 -0.48096379 1.60888440

5. Optimized geometry and the energies of 2-Aimno chalcone in presence of Carbon tetra

bromide (CBr4) at M06-2X/6-311+G(d,p) Level

S20
  SCF energy: -11044.0254857 Hartree

 Zero-point correction: 0.250593 (Hartree/Particle)

 Thermal correction to Energy: 0.274075 Hartree

 Thermal correction to Enthalpy: 0.275020 Hartree

 Thermal correction to Gibbs Free Energy: 0.187954 Hartree

 Sum of electronic and zero-point Energies: -11043.774893 Hartree

 Sum of electronic and thermal Energies: -11043.751410 Hartree

 Sum of electronic and thermal Enthalpies: -11043.750466 Hartree

 Sum of electronic and thermal Free Energies: -11043.837532 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C 1.95237015 3.25492925 0.53792004

C 2.37887818 1.93188915 0.72259605

C 1.96281315 0.96106508 -0.20571802

C 1.12866808 1.33013410 -1.26553910

C 0.72270206 2.64108520 -1.44496811

C 1.14160209 3.60366627 -0.52832804

H 2.26742417 4.00871630 1.25189910

H 0.79986906 0.55469604 -1.94834815

H 0.08167501 2.90820422 -2.27502717

H 0.82883506 4.63514536 -0.64132205

C 2.28614717 -0.50029404 -0.09300901

O 1.39346411 -1.32526710 -0.17400301

S21
C 3.68304628 -0.96156307 0.04636900

H 3.78089029 -2.01938516 0.26784202

C 4.74303836 -0.17119001 -0.17120401

H 4.56737435 0.88105407 -0.38332603

C 6.15062246 -0.58144204 -0.13382701

C 6.54457650 -1.92514515 -0.16571301

C 7.13713654 0.40781403 -0.06659401

C 7.88770758 -2.26515917 -0.11275201

H 5.79837546 -2.70590721 -0.25336502

C 8.48299065 0.06697001 -0.00784000

H 6.83846255 1.45074711 -0.05092000

C 8.86080966 -1.27078710 -0.03004100

H 8.18047960 -3.30791525 -0.14483601

H 9.23522273 0.84435807 0.05161700

H 9.90959378 -1.54038312 0.00861000

N 3.21431624 1.64083213 1.80022214

H 3.27818925 0.67274705 2.07699116

H 3.10943824 2.25989117 2.58996920

C -3.29263525 -0.33768903 0.04322900

Br -1.40721711 -0.76402506 0.01795800

Br -3.72452628 0.80487906 -1.47602311

Br -3.75013929 0.59854405 1.68742713

Br -4.34516233 -1.97172215 -0.07241301

S22
6. Optimized geometry and the energies of Azaflavanone in presence of Carbon tetra

bromide (CBr4) at M06-2X/6-311+G(d,p) Level

 SCF energy: -11043.9590698 Hartree

 Zero-point correction: 0.253757 (Hartree/Particle)

 Thermal correction to Energy: 0.275745 Hartree

 Thermal correction to Enthalpy: 0.276690 Hartree

 Thermal correction to Gibbs Free Energy: 0.195007 Hartree

 Sum of electronic and zero-point Energies: -11043.799979 Hartree

 Sum of electronic and thermal Energies: -11043.777991 Hartree

 Sum of electronic and thermal Enthalpies: -11043.777047 Hartree

 Sum of electronic and thermal Free Energies: -11043.858729 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C -3.86713300 3.45945400 0.14266900

S23
C -3.74006600 2.06349400 0.05988500

C -2.45015800 1.50428800 -0.01794100

C -1.32479300 2.33778000 -0.00483000

C -1.45836400 3.70916100 0.07963200

C -2.74242300 4.26231600 0.15067200

H -4.85682300 3.89938800 0.20265400

H -0.34796100 1.87281700 -0.07210000

H -0.58519700 4.34852000 0.08685300

H -2.86284400 5.33776700 0.21656500

C -2.28646500 0.04352400 -0.17783200

O -1.20282000 -0.50048700 -0.21894300

C -3.56729700 -0.74860800 -0.34684700

C -4.72225700 -0.13508700 0.44552500

H -3.38885300 -1.78360800 -0.05431600

H -4.46824900 -0.18364200 1.51615900

C -6.01269000 -0.88936000 0.22015900

C -6.49141500 -1.77449400 1.18339700

C -6.71796300 -0.73509700 -0.97431900

C -7.65695100 -2.50107100 0.95668700

H -5.95142900 -1.89489100 2.11713700

C -7.88398000 -1.45649400 -1.19947600

H -6.34878400 -0.04129200 -1.72196100

C -8.35554200 -2.34250000 -0.23445900

H -8.02114200 -3.18591900 1.71334800

H -8.42525900 -1.32811000 -2.12936000

H -9.26530500 -2.90384200 -0.41064900

N -4.86501600 1.25654700 0.02911100

H -3.82355400 -0.73273200 -1.41361400

S24
H -5.71002800 1.70182100 0.36182400

C 3.57272100 -0.34447900 -0.00390300

Br 1.64023600 -0.38400300 -0.08413600

Br 4.15251100 0.12715600 1.79388900

Br 4.26635100 0.96796300 -1.26215600

Br 4.28266700 -2.10012100 -0.46299400

7. Optimized geometry and the energies of Transition State (TS) of azaflavanone

formation in presence of Carbon tetra bromide (CBr4) at M06-2X/6-311+G(d,p) Level

 SCF energy: -11043.9590698 Hartree

 Zero-point correction: 0.248818 (Hartree/Particle)

 Thermal correction to Energy: 0.270313 Hartree

 Thermal correction to Enthalpy: 0.271258 Hartree

 Thermal correction to Gibbs Free Energy: 0.190463 Hartree

 Sum of electronic and zero-point Energies: -11043.710252 Hartree

 Sum of electronic and thermal Energies: -11043.688757 Hartree

 Sum of electronic and thermal Enthalpies: -11043.687812 Hartree

S25
  Sum of electronic and thermal Free Energies: -11043.768607 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C -2.30659300 2.77578000 -1.24478400

C -2.52769900 1.66999300 -0.43506800

C -1.76333500 1.42422300 0.70651000

C -0.77086100 2.33713400 1.05393500

C -0.55486300 3.46360600 0.27319600

C -1.31513600 3.67757700 -0.87657700

H -2.90064700 2.93576200 -2.13794200

H -0.17147700 2.12593800 1.93207500

H 0.21725400 4.17219300 0.54681400

H -1.13654400 4.55278300 -1.48950300

C -1.95827500 0.13109300 1.45586000

O -1.07461500 -0.26412500 2.21950600

C -3.15103800 -0.58365700 1.10465500

C -4.27254500 0.24981600 0.51332200

H -3.39708000 -1.44808500 1.71115500

H -4.54119700 1.16018100 1.06037900

C -5.51316800 -0.50862200 0.12245400

C -5.44193300 -1.81658000 -0.36250000

C -6.75768600 0.11365200 0.22044100

C -6.59918300 -2.48559300 -0.74324000

H -4.48078900 -2.31456600 -0.42435300

C -7.91634800 -0.55831800 -0.15453600

S26
H -6.82062300 1.12589600 0.60643800

C -7.83769000 -1.85935400 -0.63871200

H -6.53464000 -3.50189500 -1.11313000

H -8.87841700 -0.06863300 -0.06216400

H -8.73887800 -2.38731800 -0.92688300

N -3.51198200 0.66425300 -0.73769400

H -2.94595000 -0.40560500 -0.47498300

H -4.07391400 0.85915500 -1.56624800

C 2.99853200 -0.39872100 -0.10065000

Br 1.37299600 -0.44627500 0.94386400

Br 4.53568300 -0.78788500 1.02961000

Br 3.22113800 1.37486800 -0.88359700

Br 2.91905800 -1.71598700 -1.53615300

8. Optimized geometry and the energies of 2-Hydroxy chalcone at M06-2X/6-311+G(d,p)

Level

 SCF energy: -729.145538986 Hartree

 Zero-point correction: 0.230608 (Hartree/Particle)

 Thermal correction to Energy: 0.243758 Hartree

S27
  Thermal correction to Enthalpy: 0.244702 Hartree

 Thermal correction to Gibbs Free Energy: 0.190061 Hartree

 Sum of electronic and zero-point Energies: -728.914931 Hartree

 Sum of electronic and thermal Energies: -728.901781 Hartree

 Sum of electronic and thermal Enthalpies: -728.900837 Hartree

 Sum of electronic and thermal Free Energies: -728.955478 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C 4.08681500 -1.50654600 -0.42907600

C 4.15881000 -0.31076000 -1.14425700

C 3.21295300 0.67107800 -0.90984500

C 2.17284500 0.47927500 0.00751900

C 2.12096700 -0.72289000 0.72877900

C 3.08407200 -1.70834800 0.50347400

H 4.82419700 -2.28364900 -0.59334600

H 4.94702200 -0.14917600 -1.86833200

H 3.25347200 1.61938900 -1.43298600

H 3.02545100 -2.61957300 1.08580800

O 1.20640500 -1.00331800 1.69343500

H 0.54036300 -0.31009500 1.74865000

C 1.21999700 1.62380500 0.19250600

O 1.62561700 2.76599600 0.19101200

C -0.24062000 1.37306900 0.31483200

C -0.83938700 0.27586000 -0.17024600

S28
C -3.24043600 0.99860500 0.04193800

C -2.28170900 0.00523400 -0.19361600

C -2.71293500 -1.29842800 -0.45865800

C -4.06665400 -1.61157400 -0.46584100

C -5.00858900 -0.61931700 -0.21950400

C -4.59145200 0.68687400 0.03030100

H -2.92882900 2.02143900 0.21741800

H -1.97574100 -2.07135600 -0.64887800

H -4.38496200 -2.62743400 -0.66632300

H -6.06542300 -0.85809400 -0.22904100

H -5.32463200 1.46455600 0.20789100

H -0.21313500 -0.50868500 -0.59296000

H -0.80201400 2.20563000 0.72668900

9. Optimized geometry and the energies of Flavanone at M06-2X/6-311+G(d,p) Level

 SCF energy: -729.167044738 Hartree

 Zero-point correction: 0.232999 (Hartree/Particle)

 Thermal correction to Energy: 0.245821 Hartree

S29
  Thermal correction to Enthalpy: 0.246765 Hartree

 Thermal correction to Gibbs Free Energy: 0.192394 Hartree

 Sum of electronic and zero-point Energies: -728.934046 Hartree

 Sum of electronic and thermal Energies: -728.921224 Hartree

 Sum of electronic and thermal Enthalpies: -728.920280 Hartree

 Sum of electronic and thermal Free Energies: -728.974650 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C -3.68746300 -1.84308300 0.24407500

C -4.33513300 -0.60761000 0.13707900

C -3.58155300 0.54106200 -0.01171300

C -2.18448700 0.47679500 -0.05131400

C -1.54939000 -0.76469200 0.07511000

C -2.30593400 -1.92875400 0.21682600

H -4.27097400 -2.74939900 0.35784800

H -5.41600700 -0.55548100 0.16459000

H -4.04354500 1.51625500 -0.11618100

H -1.78990000 -2.87572000 0.31350500

O -0.19843200 -0.90096500 0.05502600

H 0.29232300 1.20411500 -1.52394600

C -1.38116200 1.69954100 -0.30191900

O -1.87008900 2.79979600 -0.39775000

C 0.10235500 1.44660600 -0.47127300

C 0.54833600 0.27009600 0.39422800

S30
C 2.94633000 0.62409400 1.02416900

C 2.01418100 -0.02974900 0.22146400

C 2.45448500 -0.90046900 -0.77309900

C 3.81630600 -1.11168200 -0.96028500

C 4.74513900 -0.45195800 -0.16179800

C 4.30783300 0.41738300 0.83206200

H 2.60543400 1.29604700 1.80591500

H 1.72759500 -1.41942900 -1.38634400

H 4.15321900 -1.79460300 -1.73126000

H 5.80536600 -0.61867500 -0.31010700

H 5.02542500 0.92885100 1.46237000

H 0.34178400 0.50013300 1.44849600

H 0.65841200 2.35177300 -0.22476700

10. Optimized geometry and the energies of 2-Hydroxy chalcone in presence of Carbon

tetra bromide (CBr4) at M06-2X/6-311+G(d,p) Level

 SCF energy: -11063.8967620 Hartree

 Zero-point correction: 0.238381 (Hartree/Particle)

 Thermal correction to Energy: 0.261360 Hartree

S31
  Thermal correction to Enthalpy: 0.262304 Hartree

 Thermal correction to Gibbs Free Energy: 0.178674 Hartree

 Sum of electronic and zero-point Energies: -11063.658381 Hartree

 Sum of electronic and thermal Energies: -11063.635402 Hartree

 Sum of electronic and thermal Enthalpies: -11063.634458 Hartree

 Sum of electronic and thermal Free Energies: -11063.718088 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C -1.05083200 2.67719500 -0.54967700

C -1.63607000 1.40964200 -0.50395400

C -1.41981800 0.58086200 0.60856200

C -0.56616600 1.03241600 1.62474700

C 0.01625000 2.28621200 1.57797800

C -0.24285200 3.11392600 0.48496600

H -1.24093500 3.29092400 -1.42188900

H -0.38157500 0.36376400 2.45774300

H 0.66463200 2.61727800 2.37874400

H 0.20430500 4.09975000 0.43069200

C -2.01622000 -0.78343200 0.78714200

O -1.38416700 -1.67338000 1.31938000

C -3.42264200 -1.05034400 0.38490400

H -3.65559300 -2.10258100 0.25762000

C -4.36581800 -0.09847500 0.33940000

H -4.06434400 0.93434000 0.50791500

C -5.79614600 -0.29577100 0.07763900

S32
C -6.40428000 -1.55669400 0.11024400

C -6.58029800 0.82336200 -0.22048300

C -7.75628400 -1.69123500 -0.16653300

H -5.82245500 -2.43294300 0.37092300

C -7.93408700 0.68789900 -0.50214500

H -6.11727400 1.80421600 -0.24075900

C -8.52437900 -0.57032600 -0.47719500

H -8.21700200 -2.67116400 -0.13231500

H -8.52657200 1.56329500 -0.73934300

H -9.58076700 -0.67995500 -0.69128200

O -2.35809600 1.06047100 -1.59902900

H -2.77115700 0.19872200 -1.47982400

C 2.91346600 -0.29679200 -0.14443200

Br 1.62039900 -1.54861700 0.55301000

Br 2.01297300 0.93934000 -1.34539600

Br 4.32020200 -1.23226200 -1.10616200

Br 3.70825200 0.70745200 1.32574800

11. Optimized geometry and the energies of Flavanone in presence of Carbon tetra

bromide (CBr4) at M06-2X/6-311+G(d,p) Level

S33
  SCF energy: -11063.9158369 Hartree

 Zero-point correction: 0.241022 (Hartree/Particle)

 Thermal correction to Energy: 0.262875 Hartree

 Thermal correction to Enthalpy: 0.263819 Hartree

 Thermal correction to Gibbs Free Energy: 0.181848 Hartree

 Sum of electronic and zero-point Energies: -11063.674719 Hartree

 Sum of electronic and thermal Energies: -11063.652866 Hartree

 Sum of electronic and thermal Enthalpies: -11063.651922 Hartree

 Sum of electronic and thermal Free Energies: -11063.733893 Hartree

Cartesian Coordinates

Charge = 0 Multiplicity = 1

C -3.86919200 3.35986600 0.20333500

C -3.71282100 1.97924900 0.07306900

C -2.43156900 1.42265600 -0.03899100

C -1.31141200 2.26223600 0.00540500

C -1.46195400 3.62838400 0.14364200

C -2.74837300 4.17136000 0.23545000

H -4.87038800 3.76306500 0.28778500

H -0.33082000 1.80960000 -0.08548000

H -0.59404500 4.27430100 0.17530600

H -2.87386400 5.24264700 0.34134900

C -2.28063800 -0.02982600 -0.28182000

O -1.20585200 -0.58164900 -0.36566400

S34
C -3.58445600 -0.77618400 -0.46187700

C -4.68162400 -0.14883000 0.39488200

H -3.44078300 -1.82857700 -0.21545800

H -4.38273400 -0.19211900 1.45110900

C -6.00444600 -0.84685400 0.21716400

C -6.30325400 -1.95452700 1.00783200

C -6.90450200 -0.44025800 -0.76543800

C -7.48768400 -2.65654600 0.81528500

H -5.60788700 -2.26742200 1.78068000

C -8.09244300 -1.13926900 -0.95256400

H -6.67706800 0.43032700 -1.36869400

C -8.38519500 -2.24909000 -0.16642900

H -7.71281800 -3.51541900 1.43609000

H -8.79207600 -0.81466100 -1.71365000

H -9.31156900 -2.79098900 -0.31418900

O -4.84304700 1.22862900 0.04945700

H -3.87555300 -0.70750400 -1.51711900

C 3.56729000 -0.33182400 -0.00284900

Br 1.64241900 -0.46305100 -0.15586200

Br 4.06637200 -0.08227600 1.86240500

Br 4.20871600 1.18694500 -1.04076800

Br 4.39719100 -1.95825700 -0.67390800

S35
HOMOs and LUMOs of 2-Amino Chalcone

Fig. S5. HOMOs of 2-Amino Chalcone with CBr4.

S36
 Fig. S6. LUMOs of 2-Amino Chalcone with CBr4

Fig. S7. LUMOs of 2- Hydroxy Chalcone with CBr4

S37
Fig. S8. HOMOs of 2- Hydroxy Chalcone with CBr4

S38
NBO ANALYSIS of 2-Aminochalcone and CBr4 complex
Summary of Natural Population Analysis: [2-Aminochalcone and CBr4 complex]

Natural Population

Natural -----------------------------------------------

Atom No Charge Core Valence Rydberg Total

-----------------------------------------------------------------------

C 1 -0.25707 1.99912 4.24065 0.01730 6.25707

C 2 0.18942 1.99898 3.79353 0.01807 5.81058

C 3 -0.20449 1.99891 4.18427 0.02131 6.20449

C 4 -0.14698 1.99914 4.13085 0.01698 6.14698

C 5 -0.24686 1.99920 4.22967 0.01799 6.24686

C 6 -0.16966 1.99922 4.15329 0.01715 6.16966

H 7 0.20989 0.00000 0.78852 0.00159 0.79011

H 8 0.22662 0.00000 0.77187 0.00151 0.77338

H 9 0.21775 0.00000 0.78104 0.00121 0.78225

H 10 0.21325 0.00000 0.78555 0.00120 0.78675

C 11 0.54162 1.99923 3.41862 0.04053 5.45838

O 12 -0.56948 1.99976 6.55397 0.01574 8.56948

C 13 -0.30268 1.99905 4.28609 0.01755 6.30268

H 14 0.21979 0.00000 0.77690 0.00332 0.78021

C 15 -0.10519 1.99910 4.08924 0.01685 6.10519

H 16 0.22340 0.00000 0.77499 0.00161 0.77660

C 17 -0.10471 1.99906 4.08799 0.01766 6.10471

C 18 -0.17544 1.99913 4.16104 0.01527 6.17544

C 19 -0.17261 1.99914 4.15723 0.01624 6.17261

C 20 -0.20395 1.99922 4.18740 0.01733 6.20395

H 21 0.21475 0.00000 0.78380 0.00145 0.78525

C 22 -0.20719 1.99921 4.19054 0.01744 6.20719

H 23 0.21585 0.00000 0.78274 0.00141 0.78415

C 24 -0.19342 1.99921 4.17683 0.01738 6.19342

H 25 0.21577 0.00000 0.78299 0.00124 0.78423

H 26 0.21586 0.00000 0.78290 0.00124 0.78414

H 27 0.21470 0.00000 0.78419 0.00111 0.78530

N 28 -0.81508 1.99947 5.79839 0.01722 7.81508

H 29 0.38856 0.00000 0.60936 0.00208 0.61144

S39
 H 30 0.38225 0.00000 0.61558 0.00217 0.61775

C 31 -0.66597 1.99984 4.61075 0.05538 6.66597

Br 32 0.21684 27.99900 6.76140 0.02276 34.78316

Br 33 0.14124 27.99902 6.84030 0.01944 34.85876

Br 34 0.14568 27.99901 6.83605 0.01926 34.85432

Br 35 0.14755 27.99901 6.83415 0.01928 34.85245

=======================================================================

* Total * 0.00000 147.98205 115.54268 0.47527 264.00000

Natural Population

--------------------------------------------------------

Core 147.98205 ( 99.9879% of 148)

Valence 115.54268 ( 99.6058% of 116)

Natural Minimal Basis 263.52473 ( 99.8200% of 264)

Natural Rydberg Basis 0.47527 ( 0.1800% of 264)

--------------------------------------------------------

Atom No Natural Electron Configuration

----------------------------------------------------------------------------

C 1 [core]2S( 0.94)2p( 3.31)4p( 0.01)

C 2 [core]2S( 0.83)2p( 2.96)4p( 0.01)

C 3 [core]2S( 0.89)2p( 3.30)4p( 0.01)

C 4 [core]2S( 0.94)2p( 3.19)4p( 0.01)

C 5 [core]2S( 0.94)2p( 3.29)4p( 0.01)

C 6 [core]2S( 0.95)2p( 3.21)4p( 0.01)

H 7 1S( 0.79)

H 8 1S( 0.77)

H 9 1S( 0.78)

H 10 1S( 0.79)

C 11 [core]2S( 0.84)2p( 2.58)3d( 0.01)4p( 0.02)

O 12 [core]2S( 1.69)2p( 4.86)3p( 0.01)3d( 0.01)

C 13 [core]2S( 0.98)2p( 3.31)4p( 0.01)

H 14 1S( 0.78)

C 15 [core]2S( 0.95)2p( 3.14)4p( 0.01)

H 16 1S( 0.77)

C 17 [core]2S( 0.88)2p( 3.21)4p( 0.01)

C 18 [core]2S( 0.94)2p( 3.22)4p( 0.01)

S40
 C 19 [core]2S( 0.94)2p( 3.22)4p( 0.01)

C 20 [core]2S( 0.95)2p( 3.24)4p( 0.01)

H 21 1S( 0.78)

C 22 [core]2S( 0.95)2p( 3.24)4p( 0.01)

H 23 1S( 0.78)

C 24 [core]2S( 0.95)2p( 3.22)4p( 0.01)

H 25 1S( 0.78)

H 26 1S( 0.78)

H 27 1S( 0.78)

N 28 [core]2S( 1.33)2p( 4.47)3p( 0.01)4p( 0.01)

H 29 1S( 0.61)

H 30 1S( 0.62)

C 31 [core]2S( 1.32)2p( 3.29)3p( 0.04)3d( 0.01)

Br 32 [core]4S( 1.87)4p( 4.89)4d( 0.01)6p( 0.01)

Br 33 [core]4S( 1.87)4p( 4.97)4d( 0.01)6p( 0.01)

Br 34 [core]4S( 1.87)4p( 4.97)4d( 0.01)6p( 0.01)

Br 35 [core]4S( 1.87)4p( 4.97)4d( 0.01)

Second Order Perturbation Theory Analysis of Fock Matrix in NBO Basis [2-Aminochalcone and
CBr4 complex]

Threshold for printing: 0.50 kcal/mol

(Intermolecular threshold: 0.05 kcal/mol)

E(2) E(j)-E(i) F(i,j)

Donor NBO (i) Acceptor NBO (j) kcal/mol a.u. a.u.

========================================================================================

within unit 1

1. BD ( 1) C 1 - C 2 /167. RY*( 1) C 3 1.20 2.09 0.045

1. BD ( 1) C 1 - C 2 /218. RY*( 1) C 6 1.18 1.90 0.042

1. BD ( 1) C 1 - C 2 /219. RY*( 2) C 6 1.64 2.13 0.053

1. BD ( 1) C 1 - C 2 /461. RY*( 2) N 28 0.70 1.70 0.031

1. BD ( 1) C 1 - C 2 /625. BD*( 1) C 1 - C 6 3.47 1.43 0.063

1. BD ( 1) C 1 - C 2 /627. BD*( 1) C 1 - H 7 1.00 1.27 0.032

1. BD ( 1) C 1 - C 2 /628. BD*( 1) C 2 - C 3 4.92 1.40 0.074

1. BD ( 1) C 1 - C 2 /630. BD*( 1) C 2 - N 28 1.38 1.27 0.037

S41
1. BD ( 1) C 1 - C 2 /632. BD*( 1) C 3 - C 11 3.89 1.26 0.063

1. BD ( 1) C 1 - C 2 /638. BD*( 1) C 6 - H 10 2.30 1.29 0.049

1. BD ( 1) C 1 - C 2 /661. BD*( 1) N 28 - H 29 2.30 1.27 0.048

2. BD ( 1) C 1 - C 6 /150. RY*( 1) C 2 0.70 2.11 0.034

2. BD ( 1) C 1 - C 6 /151. RY*( 2) C 2 1.85 2.19 0.057

2. BD ( 1) C 1 - C 6 /201. RY*( 1) C 5 1.04 1.95 0.040

2. BD ( 1) C 1 - C 6 /202. RY*( 2) C 5 1.46 2.12 0.050

2. BD ( 1) C 1 - C 6 /624. BD*( 1) C 1 - C 2 3.74 1.40 0.065

2. BD ( 1) C 1 - C 6 /627. BD*( 1) C 1 - H 7 1.47 1.28 0.039

2. BD ( 1) C 1 - C 6 /630. BD*( 1) C 2 - N 28 4.10 1.27 0.065

2. BD ( 1) C 1 - C 6 /636. BD*( 1) C 5 - C 6 3.12 1.43 0.060

2. BD ( 1) C 1 - C 6 /637. BD*( 1) C 5 - H 9 2.67 1.30 0.053

2. BD ( 1) C 1 - C 6 /638. BD*( 1) C 6 - H 10 1.02 1.29 0.032

3. BD ( 2) C 1 - C 6 /203. RY*( 3) C 5 1.37 0.78 0.032

3. BD ( 2) C 1 - C 6 /629. BD*( 2) C 2 - C 3 30.54 0.35 0.096

3. BD ( 2) C 1 - C 6 /634. BD*( 2) C 4 - C 5 21.65 0.37 0.080

4. BD ( 1) C 1 - H 7 /150. RY*( 1) C 2 1.24 1.91 0.044

4. BD ( 1) C 1 - H 7 /218. RY*( 1) C 6 1.26 1.71 0.042

4. BD ( 1) C 1 - H 7 /624. BD*( 1) C 1 - C 2 0.75 1.21 0.027

4. BD ( 1) C 1 - H 7 /625. BD*( 1) C 1 - C 6 1.13 1.24 0.033

4. BD ( 1) C 1 - H 7 /628. BD*( 1) C 2 - C 3 4.83 1.21 0.068

4. BD ( 1) C 1 - H 7 /630. BD*( 1) C 2 - N 28 0.80 1.08 0.026

4. BD ( 1) C 1 - H 7 /636. BD*( 1) C 5 - C 6 3.91 1.23 0.062

4. BD ( 1) C 1 - H 7 /638. BD*( 1) C 6 - H 10 0.64 1.10 0.024

5. BD ( 1) C 2 - C 3 /133. RY*( 1) C 1 1.37 1.91 0.046

5. BD ( 1) C 2 - C 3 /134. RY*( 2) C 1 0.68 1.99 0.033

5. BD ( 1) C 2 - C 3 /184. RY*( 1) C 4 0.92 1.93 0.038

5. BD ( 1) C 2 - C 3 /185. RY*( 2) C 4 0.62 1.91 0.031

5. BD ( 1) C 2 - C 3 /257. RY*( 3) C 11 0.71 2.34 0.037

5. BD ( 1) C 2 - C 3 /461. RY*( 2) N 28 0.57 1.70 0.028

5. BD ( 1) C 2 - C 3 /624. BD*( 1) C 1 - C 2 4.19 1.40 0.069

5. BD ( 1) C 2 - C 3 /627. BD*( 1) C 1 - H 7 2.25 1.27 0.048

5. BD ( 1) C 2 - C 3 /630. BD*( 1) C 2 - N 28 1.74 1.27 0.042

5. BD ( 1) C 2 - C 3 /631. BD*( 1) C 3 - C 4 4.81 1.41 0.074

5. BD ( 1) C 2 - C 3 /632. BD*( 1) C 3 - C 11 2.11 1.27 0.047

5. BD ( 1) C 2 - C 3 /635. BD*( 1) C 4 - H 8 2.16 1.30 0.047

5. BD ( 1) C 2 - C 3 /639. BD*( 1) C 11 - O 12 1.16 1.46 0.037

S42
5. BD ( 1) C 2 - C 3 /640. BD*( 2) C 11 - O 12 0.63 0.85 0.021

5. BD ( 1) C 2 - C 3 /662. BD*( 1) N 28 - H 30 1.89 1.27 0.044

6. BD ( 2) C 2 - C 3 /135. RY*( 3) C 1 1.57 0.79 0.035

6. BD ( 2) C 2 - C 3 /186. RY*( 3) C 4 1.52 1.40 0.045

6. BD ( 2) C 2 - C 3 /460. RY*( 1) N 28 1.86 0.88 0.040

6. BD ( 2) C 2 - C 3 /626. BD*( 2) C 1 - C 6 21.77 0.36 0.080

6. BD ( 2) C 2 - C 3 /629. BD*( 2) C 2 - C 3 1.29 0.35 0.019

6. BD ( 2) C 2 - C 3 /634. BD*( 2) C 4 - C 5 32.12 0.37 0.098

6. BD ( 2) C 2 - C 3 /639. BD*( 1) C 11 - O 12 2.63 0.97 0.050

6. BD ( 2) C 2 - C 3 /640. BD*( 2) C 11 - O 12 9.66 0.36 0.056

6. BD ( 2) C 2 - C 3 /641. BD*( 1) C 11 - C 13 1.84 0.80 0.037

6. BD ( 2) C 2 - C 3 /662. BD*( 1) N 28 - H 30 0.71 0.78 0.023

7. BD ( 1) C 2 - N 28 /133. RY*( 1) C 1 0.74 2.02 0.035

7. BD ( 1) C 2 - N 28 /167. RY*( 1) C 3 0.83 2.21 0.038

7. BD ( 1) C 2 - N 28 /624. BD*( 1) C 1 - C 2 1.63 1.52 0.045

7. BD ( 1) C 2 - N 28 /625. BD*( 1) C 1 - C 6 1.56 1.55 0.044

7. BD ( 1) C 2 - N 28 /628. BD*( 1) C 2 - C 3 1.95 1.52 0.049

7. BD ( 1) C 2 - N 28 /631. BD*( 1) C 3 - C 4 1.88 1.53 0.048

8. BD ( 1) C 3 - C 4 /151. RY*( 2) C 2 1.12 2.18 0.044

8. BD ( 1) C 3 - C 4 /201. RY*( 1) C 5 1.12 1.94 0.042

8. BD ( 1) C 3 - C 4 /202. RY*( 2) C 5 1.67 2.11 0.053

8. BD ( 1) C 3 - C 4 /255. RY*( 1) C 11 0.85 1.75 0.035

8. BD ( 1) C 3 - C 4 /628. BD*( 1) C 2 - C 3 5.15 1.39 0.076

8. BD ( 1) C 3 - C 4 /630. BD*( 1) C 2 - N 28 4.77 1.26 0.069

8. BD ( 1) C 3 - C 4 /632. BD*( 1) C 3 - C 11 2.40 1.26 0.049

8. BD ( 1) C 3 - C 4 /633. BD*( 1) C 4 - C 5 3.25 1.43 0.061

8. BD ( 1) C 3 - C 4 /635. BD*( 1) C 4 - H 8 0.94 1.29 0.031

8. BD ( 1) C 3 - C 4 /637. BD*( 1) C 5 - H 9 2.55 1.28 0.051

8. BD ( 1) C 3 - C 4 /640. BD*( 2) C 11 - O 12 1.34 0.83 0.031

8. BD ( 1) C 3 - C 4 /641. BD*( 1) C 11 - C 13 1.72 1.27 0.042

9. BD ( 1) C 3 - C 11 /150. RY*( 1) C 2 1.75 2.05 0.054

9. BD ( 1) C 3 - C 11 /184. RY*( 1) C 4 1.84 1.87 0.053

9. BD ( 1) C 3 - C 11 /272. RY*( 1) O 12 1.56 1.65 0.046

9. BD ( 1) C 3 - C 11 /289. RY*( 1) C 13 1.99 1.89 0.055

9. BD ( 1) C 3 - C 11 /624. BD*( 1) C 1 - C 2 2.82 1.34 0.055

9. BD ( 1) C 3 - C 11 /628. BD*( 1) C 2 - C 3 2.54 1.35 0.052

9. BD ( 1) C 3 - C 11 /631. BD*( 1) C 3 - C 4 2.54 1.36 0.053

S43
9. BD ( 1) C 3 - C 11 /633. BD*( 1) C 4 - C 5 2.87 1.39 0.056

9. BD ( 1) C 3 - C 11 /639. BD*( 1) C 11 - O 12 1.11 1.40 0.035

9. BD ( 1) C 3 - C 11 /641. BD*( 1) C 11 - C 13 0.74 1.23 0.027

9. BD ( 1) C 3 - C 11 /642. BD*( 1) C 13 - H 14 1.67 1.22 0.040

10. BD ( 1) C 4 - C 5 /167. RY*( 1) C 3 1.23 2.09 0.046

10. BD ( 1) C 4 - C 5 /168. RY*( 2) C 3 0.64 1.69 0.030

10. BD ( 1) C 4 - C 5 /169. RY*( 3) C 3 0.80 1.72 0.033

10. BD ( 1) C 4 - C 5 /218. RY*( 1) C 6 0.93 1.90 0.038

10. BD ( 1) C 4 - C 5 /219. RY*( 2) C 6 1.46 2.13 0.050

10. BD ( 1) C 4 - C 5 /631. BD*( 1) C 3 - C 4 3.73 1.41 0.065

10. BD ( 1) C 4 - C 5 /632. BD*( 1) C 3 - C 11 3.14 1.26 0.057

10. BD ( 1) C 4 - C 5 /635. BD*( 1) C 4 - H 8 1.23 1.29 0.036

10. BD ( 1) C 4 - C 5 /636. BD*( 1) C 5 - C 6 3.23 1.42 0.061

10. BD ( 1) C 4 - C 5 /637. BD*( 1) C 5 - H 9 1.28 1.29 0.036

10. BD ( 1) C 4 - C 5 /638. BD*( 1) C 6 - H 10 2.82 1.29 0.054

11. BD ( 2) C 4 - C 5 /220. RY*( 3) C 6 1.01 1.68 0.040

11. BD ( 2) C 4 - C 5 /626. BD*( 2) C 1 - C 6 33.75 0.35 0.098

11. BD ( 2) C 4 - C 5 /629. BD*( 2) C 2 - C 3 23.40 0.35 0.082

12. BD ( 1) C 4 - H 8 /167. RY*( 1) C 3 1.84 1.90 0.053

12. BD ( 1) C 4 - H 8 /201. RY*( 1) C 5 1.37 1.75 0.044

12. BD ( 1) C 4 - H 8 /628. BD*( 1) C 2 - C 3 5.16 1.20 0.070

12. BD ( 1) C 4 - H 8 /631. BD*( 1) C 3 - C 4 0.86 1.21 0.029

12. BD ( 1) C 4 - H 8 /633. BD*( 1) C 4 - C 5 0.93 1.24 0.030

12. BD ( 1) C 4 - H 8 /636. BD*( 1) C 5 - C 6 3.92 1.22 0.062

12. BD ( 1) C 4 - H 8 /637. BD*( 1) C 5 - H 9 0.66 1.09 0.024

13. BD ( 1) C 5 - C 6 /134. RY*( 2) C 1 1.97 1.98 0.056

13. BD ( 1) C 5 - C 6 /184. RY*( 1) C 4 0.71 1.92 0.033

13. BD ( 1) C 5 - C 6 /185. RY*( 2) C 4 1.81 1.89 0.053

13. BD ( 1) C 5 - C 6 /625. BD*( 1) C 1 - C 6 3.16 1.42 0.060

13. BD ( 1) C 5 - C 6 /627. BD*( 1) C 1 - H 7 2.95 1.26 0.055

13. BD ( 1) C 5 - C 6 /633. BD*( 1) C 4 - C 5 3.33 1.43 0.062

13. BD ( 1) C 5 - C 6 /635. BD*( 1) C 4 - H 8 3.08 1.29 0.056

13. BD ( 1) C 5 - C 6 /637. BD*( 1) C 5 - H 9 1.15 1.28 0.034

13. BD ( 1) C 5 - C 6 /638. BD*( 1) C 6 - H 10 1.03 1.28 0.032

14. BD ( 1) C 5 - H 9 /184. RY*( 1) C 4 1.26 1.73 0.042

14. BD ( 1) C 5 - H 9 /218. RY*( 1) C 6 1.27 1.70 0.042

14. BD ( 1) C 5 - H 9 /625. BD*( 1) C 1 - C 6 3.87 1.23 0.062

S44
14. BD ( 1) C 5 - H 9 /631. BD*( 1) C 3 - C 4 4.28 1.21 0.064

14. BD ( 1) C 5 - H 9 /633. BD*( 1) C 4 - C 5 1.03 1.24 0.032

14. BD ( 1) C 5 - H 9 /635. BD*( 1) C 4 - H 8 0.54 1.10 0.022

14. BD ( 1) C 5 - H 9 /636. BD*( 1) C 5 - C 6 0.82 1.22 0.028

14. BD ( 1) C 5 - H 9 /638. BD*( 1) C 6 - H 10 0.58 1.09 0.022

15. BD ( 1) C 6 - H 10 /133. RY*( 1) C 1 1.33 1.71 0.043

15. BD ( 1) C 6 - H 10 /136. RY*( 4) C 1 0.50 1.64 0.026

15. BD ( 1) C 6 - H 10 /201. RY*( 1) C 5 1.39 1.76 0.044

15. BD ( 1) C 6 - H 10 /624. BD*( 1) C 1 - C 2 4.33 1.21 0.065

15. BD ( 1) C 6 - H 10 /625. BD*( 1) C 1 - C 6 0.78 1.24 0.028

15. BD ( 1) C 6 - H 10 /627. BD*( 1) C 1 - H 7 0.66 1.08 0.024

15. BD ( 1) C 6 - H 10 /633. BD*( 1) C 4 - C 5 3.83 1.25 0.062

15. BD ( 1) C 6 - H 10 /636. BD*( 1) C 5 - C 6 0.67 1.23 0.026

15. BD ( 1) C 6 - H 10 /637. BD*( 1) C 5 - H 9 0.60 1.10 0.023

16. BD ( 1) C 11 - O 12 /168. RY*( 2) C 3 0.76 2.10 0.036

16. BD ( 1) C 11 - O 12 /255. RY*( 1) C 11 1.50 2.17 0.051

16. BD ( 1) C 11 - O 12 /289. RY*( 1) C 13 0.59 2.35 0.033

16. BD ( 1) C 11 - O 12 /628. BD*( 1) C 2 - C 3 0.96 1.81 0.037

16. BD ( 1) C 11 - O 12 /632. BD*( 1) C 3 - C 11 1.34 1.67 0.043

16. BD ( 1) C 11 - O 12 /641. BD*( 1) C 11 - C 13 1.07 1.69 0.038

16. BD ( 1) C 11 - O 12 /643. BD*( 1) C 13 - C 15 0.98 1.89 0.039

17. BD ( 2) C 11 - O 12 /292. RY*( 4) C 13 0.65 1.17 0.025

17. BD ( 2) C 11 - O 12 /628. BD*( 1) C 2 - C 3 1.30 1.07 0.033

17. BD ( 2) C 11 - O 12 /629. BD*( 2) C 2 - C 3 1.93 0.51 0.031

17. BD ( 2) C 11 - O 12 /631. BD*( 1) C 3 - C 4 0.73 1.08 0.025

17. BD ( 2) C 11 - O 12 /644. BD*( 2) C 13 - C 15 5.88 0.53 0.051

18. BD ( 1) C 11 - C 13 /168. RY*( 2) C 3 1.44 1.66 0.044

18. BD ( 1) C 11 - C 13 /272. RY*( 1) O 12 1.33 1.67 0.042

18. BD ( 1) C 11 - C 13 /311. RY*( 1) C 15 1.50 1.75 0.046

18. BD ( 1) C 11 - C 13 /631. BD*( 1) C 3 - C 4 1.38 1.38 0.039

18. BD ( 1) C 11 - C 13 /632. BD*( 1) C 3 - C 11 0.73 1.23 0.027

18. BD ( 1) C 11 - C 13 /639. BD*( 1) C 11 - O 12 0.89 1.42 0.032

18. BD ( 1) C 11 - C 13 /643. BD*( 1) C 13 - C 15 3.13 1.45 0.060

18. BD ( 1) C 11 - C 13 /646. BD*( 1) C 15 - C 17 4.18 1.29 0.066

19. BD ( 1) C 13 - H 14 /255. RY*( 1) C 11 0.67 1.58 0.029

19. BD ( 1) C 13 - H 14 /312. RY*( 2) C 15 1.32 1.58 0.041

19. BD ( 1) C 13 - H 14 /632. BD*( 1) C 3 - C 11 3.88 1.08 0.058

S45
19. BD ( 1) C 13 - H 14 /639. BD*( 1) C 11 - O 12 0.62 1.27 0.025

19. BD ( 1) C 13 - H 14 /643. BD*( 1) C 13 - C 15 1.92 1.30 0.045

19. BD ( 1) C 13 - H 14 /645. BD*( 1) C 15 - H 16 5.57 1.09 0.070

20. BD ( 1) C 13 - C 15 /255. RY*( 1) C 11 0.62 1.82 0.030

20. BD ( 1) C 13 - C 15 /256. RY*( 2) C 11 0.71 2.39 0.037

20. BD ( 1) C 13 - C 15 /257. RY*( 3) C 11 0.59 2.40 0.034

20. BD ( 1) C 13 - C 15 /258. RY*( 4) C 11 0.63 2.67 0.037

20. BD ( 1) C 13 - C 15 /334. RY*( 2) C 17 2.35 2.18 0.064

20. BD ( 1) C 13 - C 15 /639. BD*( 1) C 11 - O 12 1.83 1.51 0.047

20. BD ( 1) C 13 - C 15 /641. BD*( 1) C 11 - C 13 2.06 1.34 0.047

20. BD ( 1) C 13 - C 15 /642. BD*( 1) C 13 - H 14 1.91 1.33 0.045

20. BD ( 1) C 13 - C 15 /645. BD*( 1) C 15 - H 16 1.43 1.33 0.039

20. BD ( 1) C 13 - C 15 /646. BD*( 1) C 15 - C 17 3.27 1.38 0.060

20. BD ( 1) C 13 - C 15 /648. BD*( 1) C 17 - C 19 2.06 1.46 0.049

21. BD ( 2) C 13 - C 15 /335. RY*( 3) C 17 1.19 1.13 0.034

21. BD ( 2) C 13 - C 15 /640. BD*( 2) C 11 - O 12 24.19 0.40 0.088

21. BD ( 2) C 13 - C 15 /649. BD*( 2) C 17 - C 19 11.47 0.39 0.064

22. BD ( 1) C 15 - H 16 /290. RY*( 2) C 13 1.67 1.57 0.046

22. BD ( 1) C 15 - H 16 /333. RY*( 1) C 17 1.09 1.89 0.041

22. BD ( 1) C 15 - H 16 /641. BD*( 1) C 11 - C 13 0.70 1.10 0.025

22. BD ( 1) C 15 - H 16 /642. BD*( 1) C 13 - H 14 6.26 1.09 0.074

22. BD ( 1) C 15 - H 16 /643. BD*( 1) C 13 - C 15 1.37 1.30 0.038

22. BD ( 1) C 15 - H 16 /647. BD*( 1) C 17 - C 18 4.76 1.22 0.068

23. BD ( 1) C 15 - C 17 /289. RY*( 1) C 13 1.11 1.91 0.041

23. BD ( 1) C 15 - C 17 /290. RY*( 2) C 13 0.57 1.72 0.028

23. BD ( 1) C 15 - C 17 /350. RY*( 1) C 18 1.08 1.87 0.040

23. BD ( 1) C 15 - C 17 /367. RY*( 1) C 19 1.67 1.87 0.050

23. BD ( 1) C 15 - C 17 /641. BD*( 1) C 11 - C 13 2.99 1.25 0.055

23. BD ( 1) C 15 - C 17 /643. BD*( 1) C 13 - C 15 3.43 1.45 0.063

23. BD ( 1) C 15 - C 17 /647. BD*( 1) C 17 - C 18 3.13 1.37 0.058

23. BD ( 1) C 15 - C 17 /648. BD*( 1) C 17 - C 19 2.72 1.37 0.055

23. BD ( 1) C 15 - C 17 /650. BD*( 1) C 18 - C 20 2.09 1.39 0.048

23. BD ( 1) C 15 - C 17 /653. BD*( 1) C 19 - C 22 2.35 1.38 0.051

24. BD ( 1) C 17 - C 18 /311. RY*( 1) C 15 1.29 1.78 0.043

24. BD ( 1) C 17 - C 18 /367. RY*( 1) C 19 0.74 1.90 0.034

24. BD ( 1) C 17 - C 18 /384. RY*( 1) C 20 1.21 1.88 0.043

24. BD ( 1) C 17 - C 18 /385. RY*( 2) C 20 1.59 2.12 0.052

S46
24. BD ( 1) C 17 - C 18 /645. BD*( 1) C 15 - H 16 1.66 1.27 0.041

24. BD ( 1) C 17 - C 18 /646. BD*( 1) C 15 - C 17 3.21 1.32 0.058

24. BD ( 1) C 17 - C 18 /648. BD*( 1) C 17 - C 19 4.31 1.40 0.069

24. BD ( 1) C 17 - C 18 /650. BD*( 1) C 18 - C 20 3.46 1.42 0.063

24. BD ( 1) C 17 - C 18 /652. BD*( 1) C 18 - H 21 1.06 1.28 0.033

24. BD ( 1) C 17 - C 18 /654. BD*( 1) C 19 - H 23 2.58 1.27 0.051

24. BD ( 1) C 17 - C 18 /656. BD*( 1) C 20 - H 25 2.50 1.28 0.051

25. BD ( 1) C 17 - C 19 /311. RY*( 1) C 15 1.74 1.78 0.050

25. BD ( 1) C 17 - C 19 /350. RY*( 1) C 18 0.72 1.90 0.033

25. BD ( 1) C 17 - C 19 /351. RY*( 2) C 18 0.56 2.00 0.030

25. BD ( 1) C 17 - C 19 /406. RY*( 1) C 22 1.22 1.88 0.043

25. BD ( 1) C 17 - C 19 /407. RY*( 2) C 22 1.63 2.12 0.053

25. BD ( 1) C 17 - C 19 /643. BD*( 1) C 13 - C 15 2.00 1.48 0.049

25. BD ( 1) C 17 - C 19 /646. BD*( 1) C 15 - C 17 2.76 1.32 0.054

25. BD ( 1) C 17 - C 19 /647. BD*( 1) C 17 - C 18 4.33 1.40 0.069

25. BD ( 1) C 17 - C 19 /652. BD*( 1) C 18 - H 21 2.73 1.28 0.053

25. BD ( 1) C 17 - C 19 /653. BD*( 1) C 19 - C 22 3.22 1.42 0.060

25. BD ( 1) C 17 - C 19 /654. BD*( 1) C 19 - H 23 1.04 1.28 0.033

25. BD ( 1) C 17 - C 19 /659. BD*( 1) C 22 - H 26 2.48 1.28 0.050

26. BD ( 2) C 17 - C 19 /313. RY*( 3) C 15 0.89 1.24 0.033

26. BD ( 2) C 17 - C 19 /352. RY*( 3) C 18 1.97 1.03 0.045

26. BD ( 2) C 17 - C 19 /408. RY*( 3) C 22 0.82 0.89 0.027

26. BD ( 2) C 17 - C 19 /409. RY*( 4) C 22 0.66 1.91 0.035

26. BD ( 2) C 17 - C 19 /644. BD*( 2) C 13 - C 15 17.47 0.37 0.078

26. BD ( 2) C 17 - C 19 /651. BD*( 2) C 18 - C 20 26.81 0.36 0.089

26. BD ( 2) C 17 - C 19 /658. BD*( 2) C 22 - C 24 27.43 0.35 0.089

27. BD ( 1) C 18 - C 20 /333. RY*( 1) C 17 2.10 2.08 0.059

27. BD ( 1) C 18 - C 20 /428. RY*( 1) C 24 0.99 1.91 0.039

27. BD ( 1) C 18 - C 20 /429. RY*( 2) C 24 1.43 2.12 0.049

27. BD ( 1) C 18 - C 20 /646. BD*( 1) C 15 - C 17 4.14 1.33 0.066

27. BD ( 1) C 18 - C 20 /647. BD*( 1) C 17 - C 18 3.80 1.41 0.065

27. BD ( 1) C 18 - C 20 /652. BD*( 1) C 18 - H 21 1.22 1.29 0.035

27. BD ( 1) C 18 - C 20 /655. BD*( 1) C 20 - C 24 3.12 1.42 0.060

27. BD ( 1) C 18 - C 20 /656. BD*( 1) C 20 - H 25 1.09 1.29 0.034

27. BD ( 1) C 18 - C 20 /660. BD*( 1) C 24 - H 27 2.62 1.29 0.052

28. BD ( 2) C 18 - C 20 /430. RY*( 3) C 24 1.27 0.83 0.032

28. BD ( 2) C 18 - C 20 /649. BD*( 2) C 17 - C 19 27.62 0.36 0.090

S47
28. BD ( 2) C 18 - C 20 /658. BD*( 2) C 22 - C 24 28.83 0.36 0.091

29. BD ( 1) C 18 - H 21 /333. RY*( 1) C 17 1.02 1.89 0.039

29. BD ( 1) C 18 - H 21 /334. RY*( 2) C 17 0.89 1.94 0.037

29. BD ( 1) C 18 - H 21 /384. RY*( 1) C 20 1.20 1.69 0.040

29. BD ( 1) C 18 - H 21 /647. BD*( 1) C 17 - C 18 0.94 1.22 0.030

29. BD ( 1) C 18 - H 21 /648. BD*( 1) C 17 - C 19 4.78 1.22 0.068

29. BD ( 1) C 18 - H 21 /650. BD*( 1) C 18 - C 20 0.90 1.24 0.030

29. BD ( 1) C 18 - H 21 /655. BD*( 1) C 20 - C 24 4.05 1.23 0.063

29. BD ( 1) C 18 - H 21 /656. BD*( 1) C 20 - H 25 0.67 1.10 0.024

30. BD ( 1) C 19 - C 22 /334. RY*( 2) C 17 2.09 2.13 0.060

30. BD ( 1) C 19 - C 22 /428. RY*( 1) C 24 0.99 1.91 0.039

30. BD ( 1) C 19 - C 22 /429. RY*( 2) C 24 1.45 2.12 0.050

30. BD ( 1) C 19 - C 22 /646. BD*( 1) C 15 - C 17 3.90 1.33 0.064

30. BD ( 1) C 19 - C 22 /648. BD*( 1) C 17 - C 19 3.62 1.41 0.064

30. BD ( 1) C 19 - C 22 /654. BD*( 1) C 19 - H 23 1.13 1.28 0.034

30. BD ( 1) C 19 - C 22 /657. BD*( 1) C 22 - C 24 3.15 1.42 0.060

30. BD ( 1) C 19 - C 22 /659. BD*( 1) C 22 - H 26 1.09 1.29 0.034

30. BD ( 1) C 19 - C 22 /660. BD*( 1) C 24 - H 27 2.70 1.29 0.053

31. BD ( 1) C 19 - H 23 /333. RY*( 1) C 17 1.82 1.89 0.052

31. BD ( 1) C 19 - H 23 /406. RY*( 1) C 22 1.21 1.70 0.041

31. BD ( 1) C 19 - H 23 /647. BD*( 1) C 17 - C 18 4.97 1.22 0.070

31. BD ( 1) C 19 - H 23 /648. BD*( 1) C 17 - C 19 0.89 1.22 0.029

31. BD ( 1) C 19 - H 23 /653. BD*( 1) C 19 - C 22 0.84 1.23 0.029

31. BD ( 1) C 19 - H 23 /657. BD*( 1) C 22 - C 24 3.93 1.23 0.062

31. BD ( 1) C 19 - H 23 /659. BD*( 1) C 22 - H 26 0.65 1.09 0.024

32. BD ( 1) C 20 - C 24 /350. RY*( 1) C 18 0.92 1.91 0.037

32. BD ( 1) C 20 - C 24 /351. RY*( 2) C 18 1.57 2.01 0.050

32. BD ( 1) C 20 - C 24 /406. RY*( 1) C 22 1.05 1.89 0.040

32. BD ( 1) C 20 - C 24 /407. RY*( 2) C 22 1.51 2.12 0.051

32. BD ( 1) C 20 - C 24 /650. BD*( 1) C 18 - C 20 3.19 1.43 0.060

32. BD ( 1) C 20 - C 24 /652. BD*( 1) C 18 - H 21 2.82 1.28 0.054

32. BD ( 1) C 20 - C 24 /656. BD*( 1) C 20 - H 25 1.05 1.28 0.033

32. BD ( 1) C 20 - C 24 /657. BD*( 1) C 22 - C 24 3.00 1.42 0.058

32. BD ( 1) C 20 - C 24 /659. BD*( 1) C 22 - H 26 2.78 1.28 0.053

32. BD ( 1) C 20 - C 24 /660. BD*( 1) C 24 - H 27 1.02 1.29 0.032

33. BD ( 1) C 20 - H 25 /350. RY*( 1) C 18 1.26 1.72 0.042

33. BD ( 1) C 20 - H 25 /428. RY*( 1) C 24 1.29 1.71 0.042

S48
33. BD ( 1) C 20 - H 25 /647. BD*( 1) C 17 - C 18 4.18 1.22 0.064

33. BD ( 1) C 20 - H 25 /650. BD*( 1) C 18 - C 20 0.82 1.24 0.028

33. BD ( 1) C 20 - H 25 /652. BD*( 1) C 18 - H 21 0.63 1.09 0.024

33. BD ( 1) C 20 - H 25 /655. BD*( 1) C 20 - C 24 0.72 1.23 0.027

33. BD ( 1) C 20 - H 25 /657. BD*( 1) C 22 - C 24 3.96 1.23 0.062

33. BD ( 1) C 20 - H 25 /660. BD*( 1) C 24 - H 27 0.63 1.10 0.024

34. BD ( 1) C 22 - C 24 /367. RY*( 1) C 19 0.73 1.91 0.033

34. BD ( 1) C 22 - C 24 /368. RY*( 2) C 19 1.80 1.93 0.053

34. BD ( 1) C 22 - C 24 /384. RY*( 1) C 20 1.06 1.88 0.040

34. BD ( 1) C 22 - C 24 /385. RY*( 2) C 20 1.51 2.13 0.051

34. BD ( 1) C 22 - C 24 /653. BD*( 1) C 19 - C 22 3.21 1.42 0.060

34. BD ( 1) C 22 - C 24 /654. BD*( 1) C 19 - H 23 2.87 1.28 0.054

34. BD ( 1) C 22 - C 24 /655. BD*( 1) C 20 - C 24 2.99 1.42 0.058

34. BD ( 1) C 22 - C 24 /656. BD*( 1) C 20 - H 25 2.71 1.29 0.053

34. BD ( 1) C 22 - C 24 /659. BD*( 1) C 22 - H 26 1.10 1.29 0.034

34. BD ( 1) C 22 - C 24 /660. BD*( 1) C 24 - H 27 1.05 1.29 0.033

35. BD ( 2) C 22 - C 24 /369. RY*( 3) C 19 1.08 0.83 0.029

35. BD ( 2) C 22 - C 24 /370. RY*( 4) C 19 0.55 1.88 0.032

35. BD ( 2) C 22 - C 24 /386. RY*( 3) C 20 1.91 0.88 0.040

35. BD ( 2) C 22 - C 24 /649. BD*( 2) C 17 - C 19 30.09 0.36 0.093

35. BD ( 2) C 22 - C 24 /651. BD*( 2) C 18 - C 20 26.87 0.36 0.089

36. BD ( 1) C 22 - H 26 /367. RY*( 1) C 19 1.27 1.72 0.042

36. BD ( 1) C 22 - H 26 /428. RY*( 1) C 24 1.31 1.71 0.042

36. BD ( 1) C 22 - H 26 /648. BD*( 1) C 17 - C 19 4.11 1.22 0.063

36. BD ( 1) C 22 - H 26 /653. BD*( 1) C 19 - C 22 0.79 1.23 0.028

36. BD ( 1) C 22 - H 26 /654. BD*( 1) C 19 - H 23 0.60 1.09 0.023

36. BD ( 1) C 22 - H 26 /655. BD*( 1) C 20 - C 24 3.99 1.23 0.063

36. BD ( 1) C 22 - H 26 /657. BD*( 1) C 22 - C 24 0.78 1.23 0.028

36. BD ( 1) C 22 - H 26 /660. BD*( 1) C 24 - H 27 0.64 1.10 0.024

37. BD ( 1) C 24 - H 27 /384. RY*( 1) C 20 1.37 1.69 0.043

37. BD ( 1) C 24 - H 27 /406. RY*( 1) C 22 1.37 1.70 0.043

37. BD ( 1) C 24 - H 27 /650. BD*( 1) C 18 - C 20 4.06 1.24 0.063

37. BD ( 1) C 24 - H 27 /653. BD*( 1) C 19 - C 22 4.07 1.23 0.063

37. BD ( 1) C 24 - H 27 /655. BD*( 1) C 20 - C 24 0.70 1.23 0.026

37. BD ( 1) C 24 - H 27 /656. BD*( 1) C 20 - H 25 0.64 1.10 0.024

37. BD ( 1) C 24 - H 27 /657. BD*( 1) C 22 - C 24 0.74 1.23 0.027

37. BD ( 1) C 24 - H 27 /659. BD*( 1) C 22 - H 26 0.64 1.10 0.024

S49
38. BD ( 1) N 28 - H 29 /150. RY*( 1) C 2 0.75 2.05 0.035

38. BD ( 1) N 28 - H 29 /151. RY*( 2) C 2 1.14 2.14 0.044

38. BD ( 1) N 28 - H 29 /624. BD*( 1) C 1 - C 2 4.18 1.35 0.067

39. BD ( 1) N 28 - H 30 /150. RY*( 1) C 2 0.55 2.05 0.030

39. BD ( 1) N 28 - H 30 /151. RY*( 2) C 2 0.92 2.14 0.040

39. BD ( 1) N 28 - H 30 /153. RY*( 4) C 2 0.57 1.90 0.029

39. BD ( 1) N 28 - H 30 /628. BD*( 1) C 2 - C 3 4.66 1.35 0.071

39. BD ( 1) N 28 - H 30 /629. BD*( 2) C 2 - C 3 0.84 0.78 0.026

44. CR ( 1) C 1 /151. RY*( 2) C 2 1.77 11.80 0.129

44. CR ( 1) C 1 /219. RY*( 2) C 6 1.74 11.75 0.128

44. CR ( 1) C 1 /628. BD*( 1) C 2 - C 3 0.94 11.01 0.092

44. CR ( 1) C 1 /630. BD*( 1) C 2 - N 28 0.68 10.88 0.077

44. CR ( 1) C 1 /636. BD*( 1) C 5 - C 6 0.76 11.03 0.082

45. CR ( 1) C 2 /134. RY*( 2) C 1 1.59 11.65 0.122

45. CR ( 1) C 2 /168. RY*( 2) C 3 0.61 11.37 0.074

45. CR ( 1) C 2 /169. RY*( 3) C 3 0.51 11.39 0.068

45. CR ( 1) C 2 /624. BD*( 1) C 1 - C 2 0.63 11.07 0.075

45. CR ( 1) C 2 /625. BD*( 1) C 1 - C 6 0.67 11.10 0.077

45. CR ( 1) C 2 /628. BD*( 1) C 2 - C 3 0.67 11.07 0.077

45. CR ( 1) C 2 /631. BD*( 1) C 3 - C 4 0.71 11.08 0.080

45. CR ( 1) C 2 /632. BD*( 1) C 3 - C 11 0.83 10.94 0.086

46. CR ( 1) C 3 /150. RY*( 1) C 2 0.61 11.72 0.075

46. CR ( 1) C 3 /151. RY*( 2) C 2 1.29 11.81 0.110

46. CR ( 1) C 3 /185. RY*( 2) C 4 1.64 11.52 0.123

46. CR ( 1) C 3 /256. RY*( 2) C 11 0.71 11.95 0.082

46. CR ( 1) C 3 /624. BD*( 1) C 1 - C 2 0.71 11.02 0.079

46. CR ( 1) C 3 /630. BD*( 1) C 2 - N 28 0.90 10.89 0.089

46. CR ( 1) C 3 /631. BD*( 1) C 3 - C 4 0.64 11.03 0.075

46. CR ( 1) C 3 /633. BD*( 1) C 4 - C 5 0.73 11.06 0.080

47. CR ( 1) C 4 /168. RY*( 2) C 3 0.51 11.31 0.068

47. CR ( 1) C 4 /169. RY*( 3) C 3 0.80 11.34 0.085

47. CR ( 1) C 4 /202. RY*( 2) C 5 1.57 11.73 0.121

47. CR ( 1) C 4 /628. BD*( 1) C 2 - C 3 0.93 11.01 0.091

47. CR ( 1) C 4 /632. BD*( 1) C 3 - C 11 0.67 10.88 0.077

47. CR ( 1) C 4 /636. BD*( 1) C 5 - C 6 0.70 11.04 0.079

48. CR ( 1) C 5 /185. RY*( 2) C 4 1.02 11.51 0.097

48. CR ( 1) C 5 /188. RY*( 5) C 4 0.58 11.49 0.073

S50
48. CR ( 1) C 5 /219. RY*( 2) C 6 1.31 11.74 0.111

48. CR ( 1) C 5 /625. BD*( 1) C 1 - C 6 0.72 11.04 0.080

48. CR ( 1) C 5 /631. BD*( 1) C 3 - C 4 0.82 11.01 0.085

49. CR ( 1) C 6 /134. RY*( 2) C 1 0.88 11.60 0.090

49. CR ( 1) C 6 /136. RY*( 4) C 1 0.69 11.45 0.079

49. CR ( 1) C 6 /202. RY*( 2) C 5 1.41 11.74 0.115

49. CR ( 1) C 6 /624. BD*( 1) C 1 - C 2 0.77 11.01 0.083

49. CR ( 1) C 6 /633. BD*( 1) C 4 - C 5 0.67 11.05 0.077

50. CR ( 1) C 11 /167. RY*( 1) C 3 0.81 11.82 0.087

50. CR ( 1) C 11 /290. RY*( 2) C 13 0.69 11.47 0.079

50. CR ( 1) C 11 /628. BD*( 1) C 2 - C 3 0.65 11.12 0.076

50. CR ( 1) C 11 /643. BD*( 1) C 13 - C 15 0.71 11.21 0.080

51. CR ( 1) O 12 /255. RY*( 1) C 11 6.33 20.34 0.322

51. CR ( 1) O 12 /632. BD*( 1) C 3 - C 11 0.60 19.84 0.099

51. CR ( 1) O 12 /641. BD*( 1) C 11 - C 13 0.58 19.86 0.097

52. CR ( 1) C 13 /256. RY*( 2) C 11 0.52 11.95 0.071

52. CR ( 1) C 13 /261. RY*( 7) C 11 0.91 11.70 0.092

52. CR ( 1) C 13 /312. RY*( 2) C 15 1.36 11.39 0.111

52. CR ( 1) C 13 /313. RY*( 3) C 15 0.74 11.35 0.082

52. CR ( 1) C 13 /632. BD*( 1) C 3 - C 11 0.53 10.89 0.069

52. CR ( 1) C 13 /643. BD*( 1) C 13 - C 15 0.81 11.11 0.085

52. CR ( 1) C 13 /646. BD*( 1) C 15 - C 17 1.10 10.94 0.099

53. CR ( 1) C 15 /289. RY*( 1) C 13 1.11 11.58 0.101

53. CR ( 1) C 15 /290. RY*( 2) C 13 1.07 11.39 0.099

53. CR ( 1) C 15 /328. RY*( 1) H 16 0.55 11.65 0.072

53. CR ( 1) C 15 /333. RY*( 1) C 17 0.93 11.71 0.093

53. CR ( 1) C 15 /337. RY*( 5) C 17 0.55 11.45 0.071

53. CR ( 1) C 15 /641. BD*( 1) C 11 - C 13 0.78 10.92 0.084

53. CR ( 1) C 15 /642. BD*( 1) C 13 - H 14 0.62 10.91 0.074

53. CR ( 1) C 15 /643. BD*( 1) C 13 - C 15 0.69 11.12 0.078

53. CR ( 1) C 15 /647. BD*( 1) C 17 - C 18 0.78 11.04 0.083

53. CR ( 1) C 15 /648. BD*( 1) C 17 - C 19 0.57 11.04 0.071

54. CR ( 1) C 17 /312. RY*( 2) C 15 0.74 11.40 0.082

54. CR ( 1) C 17 /351. RY*( 2) C 18 1.39 11.64 0.114

54. CR ( 1) C 17 /368. RY*( 2) C 19 1.48 11.56 0.117

54. CR ( 1) C 17 /643. BD*( 1) C 13 - C 15 0.73 11.12 0.081

54. CR ( 1) C 17 /650. BD*( 1) C 18 - C 20 0.66 11.05 0.076

S51
54. CR ( 1) C 17 /653. BD*( 1) C 19 - C 22 0.68 11.05 0.078

55. CR ( 1) C 18 /334. RY*( 2) C 17 2.18 11.74 0.143

55. CR ( 1) C 18 /385. RY*( 2) C 20 1.66 11.74 0.124

55. CR ( 1) C 18 /646. BD*( 1) C 15 - C 17 0.96 10.94 0.092

55. CR ( 1) C 18 /648. BD*( 1) C 17 - C 19 0.80 11.03 0.084

55. CR ( 1) C 18 /655. BD*( 1) C 20 - C 24 0.75 11.03 0.081

56. CR ( 1) C 19 /333. RY*( 1) C 17 1.44 11.70 0.116

56. CR ( 1) C 19 /334. RY*( 2) C 17 0.57 11.74 0.073

56. CR ( 1) C 19 /407. RY*( 2) C 22 1.61 11.74 0.123

56. CR ( 1) C 19 /646. BD*( 1) C 15 - C 17 0.87 10.94 0.087

56. CR ( 1) C 19 /647. BD*( 1) C 17 - C 18 0.85 11.02 0.087

56. CR ( 1) C 19 /657. BD*( 1) C 22 - C 24 0.72 11.04 0.080

57. CR ( 1) C 20 /351. RY*( 2) C 18 1.22 11.63 0.106

57. CR ( 1) C 20 /429. RY*( 2) C 24 1.51 11.74 0.119

57. CR ( 1) C 20 /647. BD*( 1) C 17 - C 18 0.78 11.02 0.083

57. CR ( 1) C 20 /657. BD*( 1) C 22 - C 24 0.70 11.04 0.079

58. CR ( 1) C 22 /368. RY*( 2) C 19 1.11 11.55 0.101

58. CR ( 1) C 22 /429. RY*( 2) C 24 1.53 11.74 0.120

58. CR ( 1) C 22 /648. BD*( 1) C 17 - C 19 0.76 11.03 0.082

58. CR ( 1) C 22 /655. BD*( 1) C 20 - C 24 0.70 11.03 0.079

59. CR ( 1) C 24 /385. RY*( 2) C 20 1.38 11.74 0.114

59. CR ( 1) C 24 /407. RY*( 2) C 22 1.42 11.74 0.115

59. CR ( 1) C 24 /650. BD*( 1) C 18 - C 20 0.72 11.05 0.080

59. CR ( 1) C 24 /653. BD*( 1) C 19 - C 22 0.72 11.04 0.080

60. CR ( 1) N 28 /150. RY*( 1) C 2 2.50 15.91 0.178

60. CR ( 1) N 28 /628. BD*( 1) C 2 - C 3 0.58 15.20 0.085

118. LP ( 1) O 12 /255. RY*( 1) C 11 15.70 1.78 0.149

118. LP ( 1) O 12 /271. RY*( 17) C 11 0.60 4.19 0.045

118. LP ( 1) O 12 /632. BD*( 1) C 3 - C 11 2.64 1.28 0.052

118. LP ( 1) O 12 /641. BD*( 1) C 11 - C 13 1.02 1.30 0.033

119. LP ( 2) O 12 /256. RY*( 2) C 11 1.87 1.90 0.055

119. LP ( 2) O 12 /257. RY*( 3) C 11 1.99 1.91 0.057

119. LP ( 2) O 12 /258. RY*( 4) C 11 0.57 2.19 0.032

119. LP ( 2) O 12 /632. BD*( 1) C 3 - C 11 19.89 0.84 0.117

119. LP ( 2) O 12 /641. BD*( 1) C 11 - C 13 21.16 0.86 0.122

119. LP ( 2) O 12 /643. BD*( 1) C 13 - C 15 0.55 1.06 0.022

120. LP ( 1) N 28 /152. RY*( 3) C 2 1.80 1.96 0.055

S52
120. LP ( 1) N 28 /477. RY*( 1) H 29 0.85 2.27 0.041

120. LP ( 1) N 28 /482. RY*( 1) H 30 0.68 2.24 0.036

120. LP ( 1) N 28 /483. RY*( 2) H 30 0.51 1.62 0.027

120. LP ( 1) N 28 /629. BD*( 2) C 2 - C 3 34.24 0.42 0.115

120. LP ( 1) N 28 /644. BD*( 2) C 13 - C 15 0.54 0.44 0.014

626. BD*( 2) C 1 - C 6 /135. RY*( 3) C 1 2.93 0.42 0.078

626. BD*( 2) C 1 - C 6 /221. RY*( 4) C 6 2.38 0.72 0.091

629. BD*( 2) C 2 - C 3 /135. RY*( 3) C 1 0.84 0.43 0.037

629. BD*( 2) C 2 - C 3 /154. RY*( 5) C 2 0.57 1.31 0.053

629. BD*( 2) C 2 - C 3 /169. RY*( 3) C 3 0.62 0.89 0.045

629. BD*( 2) C 2 - C 3 /186. RY*( 3) C 4 0.50 1.05 0.045

629. BD*( 2) C 2 - C 3 /460. RY*( 1) N 28 1.32 0.52 0.051

629. BD*( 2) C 2 - C 3 /634. BD*( 2) C 4 - C 5 257.60 0.02 0.095

629. BD*( 2) C 2 - C 3 /639. BD*( 1) C 11 - O 12 1.13 0.62 0.051

629. BD*( 2) C 2 - C 3 /641. BD*( 1) C 11 - C 13 1.09 0.45 0.041

629. BD*( 2) C 2 - C 3 /644. BD*( 2) C 13 - C 15 0.76 0.02 0.007

634. BD*( 2) C 4 - C 5 /187. RY*( 4) C 4 1.83 1.01 0.096

634. BD*( 2) C 4 - C 5 /203. RY*( 3) C 5 3.42 0.41 0.084

634. BD*( 2) C 4 - C 5 /211. RY*( 11) C 5 0.60 0.55 0.041

640. BD*( 2) C 11 - O 12 /258. RY*( 4) C 11 0.81 1.77 0.121

640. BD*( 2) C 11 - O 12 /274. RY*( 3) O 12 1.63 0.54 0.095

640. BD*( 2) C 11 - O 12 /628. BD*( 1) C 2 - C 3 0.53 0.56 0.051

640. BD*( 2) C 11 - O 12 /644. BD*( 2) C 13 - C 15 57.64 0.01 0.074

649. BD*( 2) C 17 - C 19 /335. RY*( 3) C 17 0.52 0.73 0.041

649. BD*( 2) C 17 - C 19 /352. RY*( 3) C 18 0.77 0.68 0.048

649. BD*( 2) C 17 - C 19 /369. RY*( 3) C 19 4.13 0.47 0.092

649. BD*( 2) C 17 - C 19 /644. BD*( 2) C 13 - C 15 63.37 0.02 0.070

651. BD*( 2) C 18 - C 20 /352. RY*( 3) C 18 0.96 0.68 0.059

651. BD*( 2) C 18 - C 20 /354. RY*( 5) C 18 0.86 1.33 0.078

651. BD*( 2) C 18 - C 20 /386. RY*( 3) C 20 1.76 0.52 0.070

651. BD*( 2) C 18 - C 20 /387. RY*( 4) C 20 0.54 1.59 0.067

658. BD*( 2) C 22 - C 24 /386. RY*( 3) C 20 0.61 0.52 0.040

658. BD*( 2) C 22 - C 24 /408. RY*( 3) C 22 3.19 0.54 0.092

658. BD*( 2) C 22 - C 24 /416. RY*( 11) C 22 0.52 0.40 0.032

658. BD*( 2) C 22 - C 24 /430. RY*( 3) C 24 3.42 0.47 0.089

658. BD*( 2) C 22 - C 24 /438. RY*( 11) C 24 0.50 0.34 0.029

S53
from unit 1 to unit 2

17. BD ( 2) C 11 - O 12 /663. BD*( 1) C 31 -Br 32 0.06 0.52 0.005

18. BD ( 1) C 11 - C 13 /663. BD*( 1) C 31 -Br 32 0.09 0.82 0.008

118. LP ( 1) O 12 /663. BD*( 1) C 31 -Br 32 1.51 0.86 0.033

119. LP ( 2) O 12 /504. RY*( 1)Br 32 0.05 1.09 0.007

119. LP ( 2) O 12 /507. RY*( 4)Br 32 0.09 1.59 0.011

119. LP ( 2) O 12 /663. BD*( 1) C 31 -Br 32 2.78 0.43 0.031

629. BD*( 2) C 2 - C 3 /663. BD*( 1) C 31 -Br 32 0.17 0.02 0.003

from unit 2 to unit 1

40. BD ( 1) C 31 -Br 32 /255. RY*( 1) C 11 0.05 1.75 0.009

40. BD ( 1) C 31 -Br 32 /272. RY*( 1) O 12 0.41 1.69 0.024

40. BD ( 1) C 31 -Br 32 /273. RY*( 2) O 12 0.52 1.55 0.025

40. BD ( 1) C 31 -Br 32 /276. RY*( 5) O 12 0.11 2.07 0.013

121. LP ( 1)Br 32 /272. RY*( 1) O 12 0.07 2.10 0.011

121. LP ( 1)Br 32 /273. RY*( 2) O 12 0.11 1.96 0.013

121. LP ( 1)Br 32 /634. BD*( 2) C 4 - C 5 0.11 1.24 0.011

121. LP ( 1)Br 32 /639. BD*( 1) C 11 - O 12 0.08 1.84 0.011

122. LP ( 2)Br 32 /640. BD*( 2) C 11 - O 12 0.08 0.42 0.005

123. LP ( 3)Br 32 /634. BD*( 2) C 4 - C 5 0.48 0.43 0.014

within unit 2

40. BD ( 1) C 31 -Br 32 /487. RY*( 1) C 31 0.95 1.29 0.031

40. BD ( 1) C 31 -Br 32 /595. RY*( 2)Br 35 0.52 1.36 0.024

41. BD ( 1) C 31 -Br 33 /488. RY*( 2) C 31 0.61 1.30 0.025

41. BD ( 1) C 31 -Br 33 /505. RY*( 2)Br 32 0.65 1.39 0.027

42. BD ( 1) C 31 -Br 34 /489. RY*( 3) C 31 0.78 1.30 0.028

42. BD ( 1) C 31 -Br 34 /506. RY*( 3)Br 32 0.63 1.37 0.026

42. BD ( 1) C 31 -Br 34 /536. RY*( 3)Br 33 0.55 1.35 0.024

43. BD ( 1) C 31 -Br 35 /488. RY*( 2) C 31 0.61 1.30 0.025

43. BD ( 1) C 31 -Br 35 /566. RY*( 3)Br 34 0.57 1.35 0.025

63. CR ( 2)Br 32 /487. RY*( 1) C 31 1.28 63.32 0.256

64. CR ( 3)Br 32 /487. RY*( 1) C 31 5.62 12.46 0.237

64. CR ( 3)Br 32 /664. BD*( 1) C 31 -Br 33 0.90 11.97 0.095

64. CR ( 3)Br 32 /665. BD*( 1) C 31 -Br 34 0.96 11.97 0.098

64. CR ( 3)Br 32 /666. BD*( 1) C 31 -Br 35 0.93 11.98 0.097

66. CR ( 5)Br 32 /487. RY*( 1) C 31 0.61 7.59 0.061

S54
77. CR ( 2)Br 33 /488. RY*( 2) C 31 0.79 63.30 0.201

78. CR ( 3)Br 33 /488. RY*( 2) C 31 3.50 12.49 0.187

78. CR ( 3)Br 33 /489. RY*( 3) C 31 1.29 12.48 0.113

78. CR ( 3)Br 33 /663. BD*( 1) C 31 -Br 32 0.78 12.02 0.089

78. CR ( 3)Br 33 /665. BD*( 1) C 31 -Br 34 0.75 12.00 0.087

78. CR ( 3)Br 33 /666. BD*( 1) C 31 -Br 35 0.75 12.00 0.087

91. CR ( 2)Br 34 /489. RY*( 3) C 31 1.01 63.28 0.227

92. CR ( 3)Br 34 /487. RY*( 1) C 31 0.78 12.48 0.089

92. CR ( 3)Br 34 /489. RY*( 3) C 31 4.48 12.48 0.212

92. CR ( 3)Br 34 /663. BD*( 1) C 31 -Br 32 0.81 12.02 0.090

92. CR ( 3)Br 34 /664. BD*( 1) C 31 -Br 33 0.76 11.99 0.087

92. CR ( 3)Br 34 /666. BD*( 1) C 31 -Br 35 0.76 12.00 0.088

105. CR ( 2)Br 35 /488. RY*( 2) C 31 0.78 63.28 0.199

106. CR ( 3)Br 35 /487. RY*( 1) C 31 0.64 12.47 0.080

106. CR ( 3)Br 35 /488. RY*( 2) C 31 3.44 12.48 0.186

106. CR ( 3)Br 35 /489. RY*( 3) C 31 1.19 12.48 0.109

106. CR ( 3)Br 35 /663. BD*( 1) C 31 -Br 32 0.80 12.02 0.090

106. CR ( 3)Br 35 /664. BD*( 1) C 31 -Br 33 0.77 11.99 0.088

106. CR ( 3)Br 35 /665. BD*( 1) C 31 -Br 34 0.77 11.99 0.088

121. LP ( 1)Br 32 /487. RY*( 1) C 31 7.16 1.70 0.099

121. LP ( 1)Br 32 /492. RY*( 6) C 31 0.69 2.75 0.039

121. LP ( 1)Br 32 /664. BD*( 1) C 31 -Br 33 1.70 1.22 0.042

121. LP ( 1)Br 32 /665. BD*( 1) C 31 -Br 34 1.71 1.22 0.042

121. LP ( 1)Br 32 /666. BD*( 1) C 31 -Br 35 1.61 1.22 0.040

122. LP ( 2)Br 32 /489. RY*( 3) C 31 1.59 0.89 0.034

122. LP ( 2)Br 32 /491. RY*( 5) C 31 0.60 1.74 0.029

122. LP ( 2)Br 32 /664. BD*( 1) C 31 -Br 33 2.32 0.40 0.028

122. LP ( 2)Br 32 /665. BD*( 1) C 31 -Br 34 8.72 0.40 0.054

122. LP ( 2)Br 32 /666. BD*( 1) C 31 -Br 35 1.86 0.40 0.025

123. LP ( 3)Br 32 /488. RY*( 2) C 31 1.59 0.89 0.034

123. LP ( 3)Br 32 /490. RY*( 4) C 31 0.61 1.74 0.029

123. LP ( 3)Br 32 /664. BD*( 1) C 31 -Br 33 5.97 0.40 0.044

123. LP ( 3)Br 32 /666. BD*( 1) C 31 -Br 35 6.97 0.40 0.048

124. LP ( 1)Br 33 /487. RY*( 1) C 31 0.54 1.67 0.027

124. LP ( 1)Br 33 /488. RY*( 2) C 31 3.99 1.68 0.073

124. LP ( 1)Br 33 /489. RY*( 3) C 31 1.47 1.68 0.044

124. LP ( 1)Br 33 /493. RY*( 7) C 31 0.53 2.74 0.034

S55
124. LP ( 1)Br 33 /663. BD*( 1) C 31 -Br 32 1.49 1.21 0.039

124. LP ( 1)Br 33 /665. BD*( 1) C 31 -Br 34 1.27 1.19 0.035

124. LP ( 1)Br 33 /666. BD*( 1) C 31 -Br 35 1.27 1.19 0.035

125. LP ( 2)Br 33 /487. RY*( 1) C 31 1.44 0.89 0.032

125. LP ( 2)Br 33 /663. BD*( 1) C 31 -Br 32 6.16 0.43 0.047

125. LP ( 2)Br 33 /665. BD*( 1) C 31 -Br 34 2.24 0.41 0.028

125. LP ( 2)Br 33 /666. BD*( 1) C 31 -Br 35 2.00 0.41 0.026

126. LP ( 3)Br 33 /489. RY*( 3) C 31 1.11 0.90 0.028

126. LP ( 3)Br 33 /665. BD*( 1) C 31 -Br 34 5.47 0.41 0.043

126. LP ( 3)Br 33 /666. BD*( 1) C 31 -Br 35 5.71 0.41 0.044

127. LP ( 1)Br 34 /487. RY*( 1) C 31 0.97 1.67 0.036

127. LP ( 1)Br 34 /489. RY*( 3) C 31 5.10 1.68 0.083

127. LP ( 1)Br 34 /663. BD*( 1) C 31 -Br 32 1.54 1.21 0.039

127. LP ( 1)Br 34 /664. BD*( 1) C 31 -Br 33 1.28 1.19 0.036

127. LP ( 1)Br 34 /666. BD*( 1) C 31 -Br 35 1.29 1.19 0.036

128. LP ( 2)Br 34 /487. RY*( 1) C 31 1.33 0.89 0.031

128. LP ( 2)Br 34 /491. RY*( 5) C 31 0.52 1.75 0.027

128. LP ( 2)Br 34 /663. BD*( 1) C 31 -Br 32 6.38 0.43 0.048

128. LP ( 2)Br 34 /664. BD*( 1) C 31 -Br 33 1.92 0.41 0.025

128. LP ( 2)Br 34 /666. BD*( 1) C 31 -Br 35 2.40 0.41 0.028

129. LP ( 3)Br 34 /488. RY*( 2) C 31 1.55 0.90 0.034

129. LP ( 3)Br 34 /490. RY*( 4) C 31 0.56 1.75 0.028

129. LP ( 3)Br 34 /664. BD*( 1) C 31 -Br 33 5.97 0.41 0.045

129. LP ( 3)Br 34 /666. BD*( 1) C 31 -Br 35 5.39 0.41 0.043

130. LP ( 1)Br 35 /487. RY*( 1) C 31 0.80 1.67 0.033

130. LP ( 1)Br 35 /488. RY*( 2) C 31 3.93 1.68 0.073

130. LP ( 1)Br 35 /489. RY*( 3) C 31 1.36 1.68 0.043

130. LP ( 1)Br 35 /494. RY*( 8) C 31 0.53 2.78 0.034

130. LP ( 1)Br 35 /663. BD*( 1) C 31 -Br 32 1.53 1.21 0.039

130. LP ( 1)Br 35 /664. BD*( 1) C 31 -Br 33 1.29 1.19 0.036

130. LP ( 1)Br 35 /665. BD*( 1) C 31 -Br 34 1.30 1.19 0.036

131. LP ( 2)Br 35 /487. RY*( 1) C 31 1.38 0.89 0.031

131. LP ( 2)Br 35 /663. BD*( 1) C 31 -Br 32 6.30 0.43 0.047

131. LP ( 2)Br 35 /664. BD*( 1) C 31 -Br 33 1.80 0.41 0.025

131. LP ( 2)Br 35 /665. BD*( 1) C 31 -Br 34 2.57 0.41 0.029

132. LP ( 3)Br 35 /489. RY*( 3) C 31 1.15 0.90 0.029

132. LP ( 3)Br 35 /664. BD*( 1) C 31 -Br 33 6.13 0.41 0.045

S56
132. LP ( 3)Br 35 /665. BD*( 1) C 31 -Br 34 5.27 0.41 0.042

664. BD*( 1) C 31 -Br 33 /534. RY*( 1)Br 33 2.22 0.63 0.146

664. BD*( 1) C 31 -Br 33 /663. BD*( 1) C 31 -Br 32 2.24 0.02 0.021

665. BD*( 1) C 31 -Br 34 /564. RY*( 1)Br 34 2.18 0.64 0.146

665. BD*( 1) C 31 -Br 34 /569. RY*( 6)Br 34 0.53 1.16 0.098

665. BD*( 1) C 31 -Br 34 /663. BD*( 1) C 31 -Br 32 2.60 0.02 0.021

666. BD*( 1) C 31 -Br 35 /594. RY*( 1)Br 35 2.08 0.65 0.143

666. BD*( 1) C 31 -Br 35 /599. RY*( 6)Br 35 0.54 1.17 0.099

666. BD*( 1) C 31 -Br 35 /663. BD*( 1) C 31 -Br 32 2.59 0.02 0.021

Natural Bond Orbitals (Summary): [2-Aminochalcone and CBr4 complex]

Principal Delocalizations

NBO Occupancy Energy (geminal,vicinal,remote)

====================================================================================

Molecular unit 1 (C15H13NO)

1. BD ( 1) C 1 - C 2 1.97162 -0.78353 628(g),632(v),625(g),661(v)

638(v),219(v),630(g),167(v)

218(v),627(g),461(v)

2. BD ( 1) C 1 - C 6 1.97749 -0.78914 630(v),624(g),636(g),637(v)

151(v),202(v),627(g),201(v)

638(g),150(v)

3. BD ( 2) C 1 - C 6 1.70757 -0.30296 629(v),634(v),203(v)

4. BD ( 1) C 1 - H 7 1.97871 -0.59604 628(v),636(v),218(v),150(v)

625(g),630(v),624(g),638(v)

5. BD ( 1) C 2 - C 3 1.96623 -0.78793 631(g),624(g),627(v),635(v)

632(g),662(v),630(g),133(v)

639(v),184(v),257(v),134(v)

640(v),185(v),461(v)

6. BD ( 2) C 2 - C 3 1.64151 -0.30264 634(v),626(v),640(v),639(v)

460(v),641(v),135(v),186(v)

629(g),662(v)

7. BD ( 1) C 2 - N 28 1.99089 -0.90306 628(g),631(v),624(g),625(v)

167(v),133(v)

8. BD ( 1) C 3 - C 4 1.96673 -0.77480 628(g),630(v),633(g),637(v)

632(g),641(v),202(v),640(v)

S57
 151(v),201(v),635(g),255(v)

9. BD ( 1) C 3 - C 11 1.97378 -0.73177 633(v),624(v),631(g),628(g)

289(v),184(v),150(v),642(v)

272(v),639(g),641(g)

10. BD ( 1) C 4 - C 5 1.97798 -0.78364 631(g),636(g),632(v),638(v)

219(v),637(g),167(v),635(g)

218(v),169(v),168(v)

11. BD ( 2) C 4 - C 5 1.67692 -0.29437 626(v),629(v),220(v)

12. BD ( 1) C 4 - H 8 1.97804 -0.58730 628(v),636(v),167(v),201(v)

633(g),631(g),637(v),632(v)

13. BD ( 1) C 5 - C 6 1.97845 -0.77721 633(g),625(g),635(v),627(v)

134(v),185(v),637(g),638(g)

184(v)

14. BD ( 1) C 5 - H 9 1.97943 -0.58708 631(v),625(v),218(v),184(v)

633(g),636(g),638(v),635(v)

15. BD ( 1) C 6 - H 10 1.98004 -0.59330 624(v),633(v),201(v),133(v)

625(g),636(g),627(v),637(v)

16. BD ( 1) C 11 - O 12 1.99372 -1.19315 255(g),632(g),641(g),643(v)

628(v),168(v),289(v)

17. BD ( 2) C 11 - O 12 1.97093 -0.45738 644(v),629(v),628(v),631(v)

292(v),663(r)

18. BD ( 1) C 11 - C 13 1.97959 -0.75309 646(v),643(g),311(v),168(v)

631(v),272(v),639(g),632(g)

629(v),663(r)

19. BD ( 1) C 13 - H 14 1.97618 -0.60161 645(v),632(v),643(g),312(v)

255(v),639(v)

20. BD ( 1) C 13 - C 15 1.98120 -0.84604 646(g),334(v),641(g),648(v)

642(g),639(v),645(g),256(v)

258(v),255(v),257(v)

21. BD ( 2) C 13 - C 15 1.85918 -0.34268 640(v),649(v),335(v)

22. BD ( 1) C 15 - H 16 1.97222 -0.60126 642(v),647(v),290(v),643(g)

333(v),641(v)

23. BD ( 1) C 15 - C 17 1.97522 -0.75394 643(g),647(g),641(v),648(g)

653(v),650(v),367(v),289(v)

350(v),290(v)

24. BD ( 1) C 17 - C 18 1.97210 -0.78456 648(g),650(g),646(g),654(v)

656(v),645(v),385(v),311(v)

S58
 384(v),652(g),367(v)

25. BD ( 1) C 17 - C 19 1.97312 -0.78494 647(g),653(g),646(g),652(v)

659(v),643(v),311(v),407(v)

406(v),654(g),350(v),351(v)

26. BD ( 2) C 17 - C 19 1.63233 -0.30263 658(v),651(v),644(v),352(v)

313(v),408(v),409(v)

27. BD ( 1) C 18 - C 20 1.97885 -0.79563 646(v),647(g),655(g),660(v)

333(v),429(v),652(g),656(g)

428(v)

28. BD ( 2) C 18 - C 20 1.67101 -0.30770 658(v),649(v),430(v)

29. BD ( 1) C 18 - H 21 1.97937 -0.60304 648(v),655(v),384(v),333(v)

647(g),650(g),334(v),656(v)

30. BD ( 1) C 19 - C 22 1.97881 -0.79395 646(v),648(g),657(g),660(v)

334(v),429(v),654(g),659(g)

428(v)

31. BD ( 1) C 19 - H 23 1.97974 -0.60139 647(v),657(v),333(v),406(v)

648(g),653(g),659(v)

32. BD ( 1) C 20 - C 24 1.97954 -0.79123 650(g),657(g),652(v),659(v)

351(v),407(v),406(v),656(g)

660(g),350(v)

33. BD ( 1) C 20 - H 25 1.98034 -0.60097 647(v),657(v),428(v),350(v)

650(g),655(g),660(v),652(v)

34. BD ( 1) C 22 - C 24 1.97954 -0.79345 653(g),655(g),654(v),656(v)

368(v),385(v),659(g),384(v)

660(g),367(v)

35. BD ( 2) C 22 - C 24 1.65484 -0.30552 649(v),651(v),386(v),369(v)

370(v)

36. BD ( 1) C 22 - H 26 1.98032 -0.60148 648(v),655(v),428(v),367(v)

653(g),657(g),660(v),654(v)

37. BD ( 1) C 24 - H 27 1.98060 -0.60239 653(v),650(v),406(v),384(v)

657(g),655(g),659(v),656(v)

38. BD ( 1) N 28 - H 29 1.98769 -0.73603 624(v),151(v),150(v),629(v)

39. BD ( 1) N 28 - H 30 1.98663 -0.73277 628(v),629(v),151(v),153(v)

150(v)

44. CR ( 1) C 1 1.99912 -10.39656 151(v),219(v),628(v),636(v)

630(v)

45. CR ( 1) C 2 1.99898 -10.45464 134(v),632(v),631(v),628(g)

S59
 625(v),624(g),168(v),169(v)

46. CR ( 1) C 3 1.99891 -10.40630 185(v),151(v),630(v),633(v)

624(v),256(v),631(g),150(v)

47. CR ( 1) C 4 1.99915 -10.39857 202(v),628(v),169(v),636(v)

632(v),168(v)

48. CR ( 1) C 5 1.99920 -10.38948 219(v),185(v),631(v),625(v)

188(v)

49. CR ( 1) C 6 1.99922 -10.40171 202(v),134(v),624(v),136(v)

633(v)

50. CR ( 1) C 11 1.99923 -10.50903 167(v),643(v),290(v),628(v)

51. CR ( 1) O 12 1.99976 -19.35994 255(v),632(v),641(v)

52. CR ( 1) C 13 1.99905 -10.41041 312(v),646(v),261(v),643(g)

313(v),632(v),256(v)

53. CR ( 1) C 15 1.99911 -10.42407 289(v),290(v),333(v),641(v)

647(v),643(g),642(v),648(v)

328(v),337(v)

54. CR ( 1) C 17 1.99906 -10.41782 368(v),351(v),312(v),643(v)

653(v),650(v)

55. CR ( 1) C 18 1.99913 -10.40825 334(v),385(v),646(v),648(v)

655(v)

56. CR ( 1) C 19 1.99914 -10.40857 407(v),333(v),646(v),647(v)

657(v),334(v)

57. CR ( 1) C 20 1.99922 -10.40859 429(v),351(v),647(v),657(v)

58. CR ( 1) C 22 1.99921 -10.40810 429(v),368(v),648(v),655(v)

59. CR ( 1) C 24 1.99922 -10.41037 407(v),385(v),650(v),653(v)

60. CR ( 1) N 28 1.99947 -14.58765 150(v),628(v)

118. LP ( 1) O 12 1.97466 -0.79788 255(v),632(v),663(r),641(v)

271(v)

119. LP ( 2) O 12 1.89572 -0.36064 641(v),632(v),663(r),257(v)

256(v),258(v),629(r),643(r)

507(r),504(r)

120. LP ( 1) N 28 1.85345 -0.36901 629(v),152(v),477(v),482(v)

644(r),483(v)

133. RY*( 1) C 1 0.00538 1.11936

134. RY*( 2) C 1 0.00253 1.19917

135. RY*( 3) C 1 0.00114 0.48478

136. RY*( 4) C 1 0.00069 1.04616

S60
137. RY*( 5) C 1 0.00047 1.70938

138. RY*( 6) C 1 0.00031 0.67697

139. RY*( 7) C 1 0.00022 0.87356

140. RY*( 8) C 1 0.00011 1.28018

141. RY*( 9) C 1 0.00009 3.49081

142. RY*( 10) C 1 0.00006 1.08602

143. RY*( 11) C 1 0.00004 3.21380

144. RY*( 12) C 1 0.00003 2.21730

145. RY*( 13) C 1 0.00001 2.51971

146. RY*( 14) C 1 0.00000 1.53574

147. RY*( 15) C 1 0.00000 21.39969

148. RY*( 16) C 1 0.00001 1.83842

149. RY*( 17) C 1 0.00001 2.37904

150. RY*( 1) C 2 0.00475 1.31794

151. RY*( 2) C 2 0.00372 1.40497

152. RY*( 3) C 2 0.00234 1.59148

153. RY*( 4) C 2 0.00109 1.16644

154. RY*( 5) C 2 0.00101 1.35738

155. RY*( 6) C 2 0.00045 0.91427

156. RY*( 7) C 2 0.00035 1.46341

157. RY*( 8) C 2 0.00019 1.49240

158. RY*( 9) C 2 0.00016 1.98945

159. RY*( 10) C 2 0.00010 2.17609

160. RY*( 11) C 2 0.00009 3.32925

161. RY*( 12) C 2 0.00006 1.51689

162. RY*( 13) C 2 0.00007 2.24850

163. RY*( 14) C 2 0.00002 1.09602

164. RY*( 15) C 2 0.00002 2.54786

165. RY*( 16) C 2 0.00000 2.83070

166. RY*( 17) C 2 0.00001 20.42634

167. RY*( 1) C 3 0.00683 1.30987

168. RY*( 2) C 3 0.00473 0.91061

169. RY*( 3) C 3 0.00226 0.93799

170. RY*( 4) C 3 0.00123 0.93575

171. RY*( 5) C 3 0.00114 0.69163

172. RY*( 6) C 3 0.00072 0.36205

173. RY*( 7) C 3 0.00064 1.10963

S61
174. RY*( 8) C 3 0.00051 1.25928

175. RY*( 9) C 3 0.00023 1.61031

176. RY*( 10) C 3 0.00021 2.73869

177. RY*( 11) C 3 0.00017 3.09328

178. RY*( 12) C 3 0.00012 1.91102

179. RY*( 13) C 3 0.00009 2.57727

180. RY*( 14) C 3 0.00006 2.66459

181. RY*( 15) C 3 0.00004 3.17411

182. RY*( 16) C 3 0.00001 2.80589

183. RY*( 17) C 3 0.00001 21.38487

184. RY*( 1) C 4 0.00621 1.14196

185. RY*( 2) C 4 0.00252 1.11712

186. RY*( 3) C 4 0.00115 1.09903

187. RY*( 4) C 4 0.00068 1.07766

188. RY*( 5) C 4 0.00062 1.09966

189. RY*( 6) C 4 0.00027 0.92423

190. RY*( 7) C 4 0.00015 1.74374

191. RY*( 8) C 4 0.00013 2.25887

192. RY*( 9) C 4 0.00010 2.03454

193. RY*( 10) C 4 0.00007 1.54240

194. RY*( 11) C 4 0.00006 2.15835

195. RY*( 12) C 4 0.00003 2.13060

196. RY*( 13) C 4 0.00003 1.37581

197. RY*( 14) C 4 0.00003 2.38499

198. RY*( 15) C 4 0.00000 2.88680

199. RY*( 16) C 4 0.00000 2.63888

200. RY*( 17) C 4 0.00000 21.39475

201. RY*( 1) C 5 0.00575 1.16564

202. RY*( 2) C 5 0.00220 1.33451

203. RY*( 3) C 5 0.00145 0.47512

204. RY*( 4) C 5 0.00050 1.64596

205. RY*( 5) C 5 0.00040 1.32695

206. RY*( 6) C 5 0.00030 0.98793

207. RY*( 7) C 5 0.00015 0.81042

208. RY*( 8) C 5 0.00008 2.01693

209. RY*( 9) C 5 0.00005 1.78971

210. RY*( 10) C 5 0.00006 2.82047

S62
211. RY*( 11) C 5 0.00003 0.61938

212. RY*( 12) C 5 0.00002 2.53990

213. RY*( 13) C 5 0.00001 2.95977

214. RY*( 14) C 5 0.00001 2.22030

215. RY*( 15) C 5 0.00000 21.38326

216. RY*( 16) C 5 0.00001 2.54214

217. RY*( 17) C 5 0.00001 1.64695

218. RY*( 1) C 6 0.00569 1.11538

219. RY*( 2) C 6 0.00227 1.34857

220. RY*( 3) C 6 0.00083 1.38603

221. RY*( 4) C 6 0.00064 0.77525

222. RY*( 5) C 6 0.00044 1.23691

223. RY*( 6) C 6 0.00030 0.86228

224. RY*( 7) C 6 0.00014 1.96892

225. RY*( 8) C 6 0.00008 1.50013

226. RY*( 9) C 6 0.00006 2.48384

227. RY*( 10) C 6 0.00002 1.10514

228. RY*( 11) C 6 0.00002 1.79495

229. RY*( 12) C 6 0.00002 2.07733

230. RY*( 13) C 6 0.00001 2.52024

231. RY*( 14) C 6 0.00000 21.97955

232. RY*( 15) C 6 0.00000 2.47751

233. RY*( 16) C 6 0.00001 1.31845

234. RY*( 17) C 6 0.00000 2.04599

235. RY*( 1) H 7 0.00085 0.89134

236. RY*( 2) H 7 0.00018 2.08544

237. RY*( 3) H 7 0.00012 1.66233

238. RY*( 4) H 7 0.00007 2.03329

239. RY*( 5) H 7 0.00003 2.49195

240. RY*( 1) H 8 0.00070 1.24385

241. RY*( 2) H 8 0.00027 1.85241

242. RY*( 3) H 8 0.00010 1.68006

243. RY*( 4) H 8 0.00007 2.03518

244. RY*( 5) H 8 0.00004 2.60253

245. RY*( 1) H 9 0.00047 0.86968

246. RY*( 2) H 9 0.00019 2.19412

247. RY*( 3) H 9 0.00012 1.66523

S63
248. RY*( 4) H 9 0.00008 2.02992

249. RY*( 5) H 9 0.00003 2.50793

250. RY*( 1) H 10 0.00048 0.75106

251. RY*( 2) H 10 0.00017 2.26100

252. RY*( 3) H 10 0.00011 1.64018

253. RY*( 4) H 10 0.00008 2.01300

254. RY*( 5) H 10 0.00003 2.51559

255. RY*( 1) C 11 0.01533 0.97742

256. RY*( 2) C 11 0.00557 1.54413

257. RY*( 3) C 11 0.00413 1.55390

258. RY*( 4) C 11 0.00248 1.82560

259. RY*( 5) C 11 0.00159 1.17673

260. RY*( 6) C 11 0.00084 1.77119

261. RY*( 7) C 11 0.00055 1.29271

262. RY*( 8) C 11 0.00025 0.83201

263. RY*( 9) C 11 0.00019 2.64392

264. RY*( 10) C 11 0.00010 2.06688

265. RY*( 11) C 11 0.00007 3.72538

266. RY*( 12) C 11 0.00005 0.99719

267. RY*( 13) C 11 0.00003 0.91880

268. RY*( 14) C 11 0.00004 1.80796

269. RY*( 15) C 11 0.00001 19.04821

270. RY*( 16) C 11 0.00001 2.63043

271. RY*( 17) C 11 0.00001 3.38852

272. RY*( 1) O 12 0.00517 0.92022

273. RY*( 2) O 12 0.00141 0.78059

274. RY*( 3) O 12 0.00129 0.59919

275. RY*( 4) O 12 0.00053 1.38845

276. RY*( 5) O 12 0.00014 1.30315

277. RY*( 6) O 12 0.00008 1.28587

278. RY*( 7) O 12 0.00003 1.49118

279. RY*( 8) O 12 0.00004 4.73224

280. RY*( 9) O 12 0.00003 1.22334

281. RY*( 10) O 12 0.00002 3.25467

282. RY*( 11) O 12 0.00000 5.13130

283. RY*( 12) O 12 0.00000 5.07210

284. RY*( 13) O 12 0.00001 4.06701

S64
285. RY*( 14) O 12 0.00001 2.98264

286. RY*( 15) O 12 0.00000 2.93563

287. RY*( 16) O 12 0.00000 49.44846

288. RY*( 17) O 12 0.00000 3.12921

289. RY*( 1) C 13 0.00443 1.15594

290. RY*( 2) C 13 0.00400 0.96518

291. RY*( 3) C 13 0.00161 0.99638

292. RY*( 4) C 13 0.00095 0.70988

293. RY*( 5) C 13 0.00031 2.48311

294. RY*( 6) C 13 0.00026 0.81994

295. RY*( 7) C 13 0.00017 1.44912

296. RY*( 8) C 13 0.00013 1.37943

297. RY*( 9) C 13 0.00010 1.69986

298. RY*( 10) C 13 0.00008 2.24813

299. RY*( 11) C 13 0.00006 2.22905

300. RY*( 12) C 13 0.00004 1.97447

301. RY*( 13) C 13 0.00003 2.31736

302. RY*( 14) C 13 0.00000 2.90050

303. RY*( 15) C 13 0.00001 1.91991

304. RY*( 16) C 13 0.00001 3.46223

305. RY*( 17) C 13 0.00000 20.05699

306. RY*( 1) H 14 0.00255 0.48559

307. RY*( 2) H 14 0.00028 2.43602

308. RY*( 3) H 14 0.00008 2.02287

309. RY*( 4) H 14 0.00006 1.67461

310. RY*( 5) H 14 0.00004 2.60010

311. RY*( 1) C 15 0.00622 0.99592

312. RY*( 2) C 15 0.00291 0.97821

313. RY*( 3) C 15 0.00166 0.93612

314. RY*( 4) C 15 0.00079 1.06793

315. RY*( 5) C 15 0.00047 1.25535

316. RY*( 6) C 15 0.00025 0.94875

317. RY*( 7) C 15 0.00014 1.98240

318. RY*( 8) C 15 0.00012 4.34939

319. RY*( 9) C 15 0.00012 1.46702

320. RY*( 10) C 15 0.00012 2.09229

321. RY*( 11) C 15 0.00007 1.18032

S65
322. RY*( 12) C 15 0.00004 2.91656

323. RY*( 13) C 15 0.00003 4.42021

324. RY*( 14) C 15 0.00002 2.24862

325. RY*( 15) C 15 0.00000 14.63682

326. RY*( 16) C 15 0.00000 2.93408

327. RY*( 17) C 15 0.00001 4.80120

328. RY*( 1) H 16 0.00096 1.22439

329. RY*( 2) H 16 0.00011 1.96340

330. RY*( 3) H 16 0.00009 2.07119

331. RY*( 4) H 16 0.00007 1.82659

332. RY*( 5) H 16 0.00004 2.25973

333. RY*( 1) C 17 0.00729 1.28650

334. RY*( 2) C 17 0.00500 1.33311

335. RY*( 3) C 17 0.00136 0.78275

336. RY*( 4) C 17 0.00065 1.56326

337. RY*( 5) C 17 0.00057 1.02791

338. RY*( 6) C 17 0.00033 1.66158

339. RY*( 7) C 17 0.00031 1.53114

340. RY*( 8) C 17 0.00015 1.79586

341. RY*( 9) C 17 0.00011 2.29956

342. RY*( 10) C 17 0.00008 2.82543

343. RY*( 11) C 17 0.00008 2.55839

344. RY*( 12) C 17 0.00006 2.11370

345. RY*( 13) C 17 0.00006 4.81747

346. RY*( 14) C 17 0.00003 1.38987

347. RY*( 15) C 17 0.00001 0.64724

348. RY*( 16) C 17 0.00000 2.75102

349. RY*( 17) C 17 0.00000 19.26592

350. RY*( 1) C 18 0.00527 1.11453

351. RY*( 2) C 18 0.00216 1.21979

352. RY*( 3) C 18 0.00077 0.73137

353. RY*( 4) C 18 0.00060 1.14202

354. RY*( 5) C 18 0.00053 1.38191

355. RY*( 6) C 18 0.00024 1.07136

356. RY*( 7) C 18 0.00014 3.01157

357. RY*( 8) C 18 0.00011 1.80777

358. RY*( 9) C 18 0.00009 1.84221

S66
359. RY*( 10) C 18 0.00005 2.32266

360. RY*( 11) C 18 0.00002 1.05192

361. RY*( 12) C 18 0.00002 1.80421

362. RY*( 13) C 18 0.00001 2.08154

363. RY*( 14) C 18 0.00000 21.59124

364. RY*( 15) C 18 0.00000 1.46392

365. RY*( 16) C 18 0.00000 2.78016

366. RY*( 17) C 18 0.00000 1.83880

367. RY*( 1) C 19 0.00570 1.11693

368. RY*( 2) C 19 0.00217 1.13882

369. RY*( 3) C 19 0.00096 0.52438

370. RY*( 4) C 19 0.00063 1.57250

371. RY*( 5) C 19 0.00056 1.11964

372. RY*( 6) C 19 0.00024 0.83872

373. RY*( 7) C 19 0.00017 1.26885

374. RY*( 8) C 19 0.00013 3.61591

375. RY*( 9) C 19 0.00007 2.03293

376. RY*( 10) C 19 0.00007 1.64645

377. RY*( 11) C 19 0.00003 1.72026

378. RY*( 12) C 19 0.00003 1.33554

379. RY*( 13) C 19 0.00001 2.70081

380. RY*( 14) C 19 0.00001 1.65412

381. RY*( 15) C 19 0.00000 2.80789

382. RY*( 16) C 19 0.00000 21.30226

383. RY*( 17) C 19 0.00000 1.73267

384. RY*( 1) C 20 0.00589 1.09124

385. RY*( 2) C 20 0.00221 1.33410

386. RY*( 3) C 20 0.00068 0.57379

387. RY*( 4) C 20 0.00057 1.64310

388. RY*( 5) C 20 0.00048 1.15817

389. RY*( 6) C 20 0.00031 0.96831

390. RY*( 7) C 20 0.00015 1.78573

391. RY*( 8) C 20 0.00005 2.85846

392. RY*( 9) C 20 0.00006 1.26576

393. RY*( 10) C 20 0.00002 2.07334

394. RY*( 11) C 20 0.00001 0.40998

395. RY*( 12) C 20 0.00000 2.74942

S67
396. RY*( 13) C 20 0.00000 1.67885

397. RY*( 14) C 20 0.00000 2.66196

398. RY*( 15) C 20 0.00000 1.55152

399. RY*( 16) C 20 0.00000 22.18182

400. RY*( 17) C 20 0.00000 1.64811

401. RY*( 1) H 21 0.00070 1.28321

402. RY*( 2) H 21 0.00020 1.67110

403. RY*( 3) H 21 0.00010 1.66224

404. RY*( 4) H 21 0.00007 2.04611

405. RY*( 5) H 21 0.00004 2.50075

406. RY*( 1) C 22 0.00594 1.09739

407. RY*( 2) C 22 0.00221 1.33102

408. RY*( 3) C 22 0.00072 0.58742

409. RY*( 4) C 22 0.00054 1.60352

410. RY*( 5) C 22 0.00048 1.20851

411. RY*( 6) C 22 0.00032 0.93816

412. RY*( 7) C 22 0.00014 1.72431

413. RY*( 8) C 22 0.00007 1.78813

414. RY*( 9) C 22 0.00005 2.38271

415. RY*( 10) C 22 0.00002 2.14154

416. RY*( 11) C 22 0.00001 0.45198

417. RY*( 12) C 22 0.00000 2.74635

418. RY*( 13) C 22 0.00000 1.97374

419. RY*( 14) C 22 0.00000 1.53060

420. RY*( 15) C 22 0.00000 2.19405

421. RY*( 16) C 22 0.00000 22.12414

422. RY*( 17) C 22 0.00001 1.81325

423. RY*( 1) H 23 0.00069 0.98670

424. RY*( 2) H 23 0.00018 2.05087

425. RY*( 3) H 23 0.00010 1.63933

426. RY*( 4) H 23 0.00008 2.02512

427. RY*( 5) H 23 0.00003 2.48580

428. RY*( 1) C 24 0.00585 1.11346

429. RY*( 2) C 24 0.00211 1.32691

430. RY*( 3) C 24 0.00084 0.52195

431. RY*( 4) C 24 0.00057 1.67762

432. RY*( 5) C 24 0.00045 0.78518

S68
433. RY*( 6) C 24 0.00038 1.26092

434. RY*( 7) C 24 0.00017 1.42162

435. RY*( 8) C 24 0.00006 2.91736

436. RY*( 9) C 24 0.00005 1.73782

437. RY*( 10) C 24 0.00000 22.37975

438. RY*( 11) C 24 0.00000 0.39514

439. RY*( 12) C 24 0.00000 2.75344

440. RY*( 13) C 24 0.00001 2.58924

441. RY*( 14) C 24 0.00000 1.56767

442. RY*( 15) C 24 0.00001 1.83760

443. RY*( 16) C 24 0.00001 1.62083

444. RY*( 17) C 24 0.00000 1.74205

445. RY*( 1) H 25 0.00054 0.74794

446. RY*( 2) H 25 0.00017 2.25305

447. RY*( 3) H 25 0.00010 1.63163

448. RY*( 4) H 25 0.00008 2.00844

449. RY*( 5) H 25 0.00003 2.49933

450. RY*( 1) H 26 0.00054 0.74213

451. RY*( 2) H 26 0.00017 2.24695

452. RY*( 3) H 26 0.00010 1.62880

453. RY*( 4) H 26 0.00008 2.00562

454. RY*( 5) H 26 0.00002 2.50110

455. RY*( 1) H 27 0.00042 0.73918

456. RY*( 2) H 27 0.00017 2.26303

457. RY*( 3) H 27 0.00010 1.62742

458. RY*( 4) H 27 0.00008 2.00054

459. RY*( 5) H 27 0.00002 2.48823

460. RY*( 1) N 28 0.00377 0.57435

461. RY*( 2) N 28 0.00202 0.91564

462. RY*( 3) N 28 0.00027 0.56982

463. RY*( 4) N 28 0.00020 1.22194

464. RY*( 5) N 28 0.00012 0.87855

465. RY*( 6) N 28 0.00011 1.00388

466. RY*( 7) N 28 0.00008 1.10784

467. RY*( 8) N 28 0.00005 1.94489

468. RY*( 9) N 28 0.00003 2.31181

469. RY*( 10) N 28 0.00001 2.73123

S69
470. RY*( 11) N 28 0.00001 3.68770

471. RY*( 12) N 28 0.00001 3.86070

472. RY*( 13) N 28 0.00001 2.38650

473. RY*( 14) N 28 0.00001 2.36621

474. RY*( 15) N 28 0.00000 35.25698

475. RY*( 16) N 28 0.00001 2.36267

476. RY*( 17) N 28 0.00000 4.37871

477. RY*( 1) H 29 0.00075 1.89974

478. RY*( 2) H 29 0.00066 1.25262

479. RY*( 3) H 29 0.00016 1.96865

480. RY*( 4) H 29 0.00014 1.74185

481. RY*( 5) H 29 0.00003 2.41228

482. RY*( 1) H 30 0.00087 1.87316

483. RY*( 2) H 30 0.00060 1.24748

484. RY*( 3) H 30 0.00020 1.57018

485. RY*( 4) H 30 0.00015 2.12020

486. RY*( 5) H 30 0.00002 2.41852

624. BD*( 1) C 1 - C 2 0.02309 0.61273

625. BD*( 1) C 1 - C 6 0.01438 0.64693

626. BD*( 2) C 1 - C 6 0.32496 0.05982 634(v),629(v),135(g),221(g)

627. BD*( 1) C 1 - H 7 0.01343 0.48603

628. BD*( 1) C 2 - C 3 0.03176 0.61546

629. BD*( 2) C 2 - C 3 0.42115 0.05073 626(v),634(v),640(v),460(v)

639(v),641(v),135(v),644(r)

169(g),154(g),186(v),663(r)

630. BD*( 1) C 2 - N 28 0.01954 0.48516

631. BD*( 1) C 3 - C 4 0.02063 0.62496

632. BD*( 1) C 3 - C 11 0.06286 0.48095

633. BD*( 1) C 4 - C 5 0.01544 0.65328

634. BD*( 2) C 4 - C 5 0.31686 0.06700 626(v),629(v),663(r),203(g)

187(g),211(g)

635. BD*( 1) C 4 - H 8 0.01340 0.51032

636. BD*( 1) C 5 - C 6 0.01650 0.63666

637. BD*( 1) C 5 - H 9 0.01380 0.50759

638. BD*( 1) C 6 - H 10 0.01313 0.50366

639. BD*( 1) C 11 - O 12 0.01323 0.66716

640. BD*( 2) C 11 - O 12 0.15391 0.05767 629(v),644(v),274(g),258(g)

S70
 663(r)

641. BD*( 1) C 11 - C 13 0.05243 0.49853

642. BD*( 1) C 13 - H 14 0.01739 0.48646

643. BD*( 1) C 13 - C 15 0.01345 0.69887

644. BD*( 2) C 13 - C 15 0.09149 0.07222

645. BD*( 1) C 15 - H 16 0.01667 0.48781

646. BD*( 1) C 15 - C 17 0.02514 0.53426

647. BD*( 1) C 17 - C 18 0.02641 0.61517

648. BD*( 1) C 17 - C 19 0.02281 0.61706

649. BD*( 2) C 17 - C 19 0.36836 0.04977 658(v),651(v),644(v),369(g)

352(v),335(g)

650. BD*( 1) C 18 - C 20 0.01512 0.63614

651. BD*( 2) C 18 - C 20 0.30035 0.05384 658(v),649(v),386(g),352(g)

354(g),387(g)

652. BD*( 1) C 18 - H 21 0.01417 0.49251

653. BD*( 1) C 19 - C 22 0.01501 0.63065

654. BD*( 1) C 19 - H 23 0.01370 0.49016

655. BD*( 1) C 20 - C 24 0.01649 0.62432

656. BD*( 1) C 20 - H 25 0.01364 0.49360

657. BD*( 1) C 22 - C 24 0.01635 0.62904

658. BD*( 2) C 22 - C 24 0.32160 0.05122 649(v),651(v),430(g),408(g)

386(v),416(g),438(g)

659. BD*( 1) C 22 - H 26 0.01364 0.49353

660. BD*( 1) C 24 - H 27 0.01347 0.49504

661. BD*( 1) N 28 - H 29 0.00764 0.48357

662. BD*( 1) N 28 - H 30 0.00820 0.48023

-------------------------------

Total Lewis 114.85845 ( 97.3498%)

Valence non-Lewis 2.89158 ( 2.4508%)

Rydberg non-Lewis 0.23531 ( 0.1994%)

-------------------------------

Total unit 1 117.98533 (100.0000%)

Charge unit 1 0.01467

Molecular unit 2 (CBr4)

40. BD ( 1) C 31 -Br 32 1.98861 -0.76962 487(g),273(r),595(v),272(r)

276(r),255(r)

S71
41. BD ( 1) C 31 -Br 33 1.98977 -0.76658 505(v),488(g)

42. BD ( 1) C 31 -Br 34 1.98983 -0.76888 489(g),506(v),536(v)

43. BD ( 1) C 31 -Br 35 1.98977 -0.76774 488(g),566(v)

61. CR ( 1) C 31 1.99984 -10.69017

62. CR ( 1)Br 32 2.00000 -482.48311

63. CR ( 2)Br 32 2.00000 -62.79850 487(v)

64. CR ( 3)Br 32 1.99960 -11.93059 487(v),665(v),666(v),664(v)

65. CR ( 4)Br 32 2.00000 -56.95114

66. CR ( 5)Br 32 1.99974 -7.06157 487(v)

67. CR ( 6)Br 32 2.00000 -56.94837

68. CR ( 7)Br 32 1.99997 -7.05360

69. CR ( 8)Br 32 2.00000 -56.94824

70. CR ( 9)Br 32 1.99999 -7.05330

71. CR ( 10)Br 32 1.99992 -2.88344

72. CR ( 11)Br 32 1.99994 -2.88293

73. CR ( 12)Br 32 1.99999 -2.87254

74. CR ( 13)Br 32 1.99988 -2.88364

75. CR ( 14)Br 32 1.99995 -2.87595

76. CR ( 1)Br 33 2.00000 -482.54613

77. CR ( 2)Br 33 2.00000 -62.76977 488(v)

78. CR ( 3)Br 33 1.99959 -11.95099 488(v),489(v),663(v),666(v)

665(v)

79. CR ( 4)Br 33 2.00000 -56.94990

80. CR ( 5)Br 33 1.99998 -7.06194

81. CR ( 6)Br 33 2.00000 -56.95075

82. CR ( 7)Br 33 1.99991 -7.06437

83. CR ( 8)Br 33 2.00000 -56.95150

84. CR ( 9)Br 33 1.99985 -7.06652

85. CR ( 10)Br 33 1.99997 -2.88173

86. CR ( 11)Br 33 1.99995 -2.88460

87. CR ( 12)Br 33 1.99988 -2.88798

88. CR ( 13)Br 33 1.99997 -2.88175

89. CR ( 14)Br 33 1.99993 -2.88771

90. CR ( 1)Br 34 2.00000 -482.56295

91. CR ( 2)Br 34 2.00000 -62.75118 489(v)

92. CR ( 3)Br 34 1.99959 -11.95084 489(v),663(v),666(v),664(v)

487(v)

S72
93. CR ( 4)Br 34 2.00000 -56.94970

94. CR ( 5)Br 34 1.99998 -7.06212

95. CR ( 6)Br 34 2.00000 -56.95021

96. CR ( 7)Br 34 1.99993 -7.06359

97. CR ( 8)Br 34 2.00000 -56.95158

98. CR ( 9)Br 34 1.99982 -7.06751

99. CR ( 10)Br 34 1.99998 -2.88057

100. CR ( 11)Br 34 1.99994 -2.88579

101. CR ( 12)Br 34 1.99989 -2.88785

102. CR ( 13)Br 34 1.99998 -2.88056

103. CR ( 14)Br 34 1.99991 -2.88891

104. CR ( 1)Br 35 2.00000 -482.57053

105. CR ( 2)Br 35 2.00000 -62.74277 488(v)

106. CR ( 3)Br 35 1.99959 -11.94912 488(v),489(v),663(v),665(v)

664(v),487(v)

107. CR ( 4)Br 35 2.00000 -56.94931

108. CR ( 5)Br 35 1.99992 -7.06347

109. CR ( 6)Br 35 2.00000 -56.95052

110. CR ( 7)Br 35 1.99982 -7.06693

111. CR ( 8)Br 35 2.00000 -56.94852

112. CR ( 9)Br 35 1.99999 -7.06123

113. CR ( 10)Br 35 1.99988 -2.88758

114. CR ( 11)Br 35 1.99998 -2.87982

115. CR ( 12)Br 35 1.99996 -2.88439

116. CR ( 13)Br 35 1.99993 -2.88745

117. CR ( 14)Br 35 1.99995 -2.88041

121. LP ( 1)Br 32 1.98510 -1.17628 487(v),665(v),664(v),666(v)

492(v),634(r),273(r),639(r)

272(r)

122. LP ( 2)Br 32 1.94607 -0.35862 665(v),664(v),666(v),489(v)

491(v),640(r)

123. LP ( 3)Br 32 1.94456 -0.35811 666(v),664(v),488(v),490(v)

634(r)

124. LP ( 1)Br 33 1.98828 -1.14464 488(v),663(v),489(v),666(v)

665(v),493(v),487(v)

125. LP ( 2)Br 33 1.95757 -0.36759 663(v),665(v),666(v),487(v)

126. LP ( 3)Br 33 1.95409 -0.36651 666(v),665(v),489(v)

S73
127. LP ( 1)Br 34 1.98813 -1.14522 489(v),663(v),666(v),664(v)

487(v)

128. LP ( 2)Br 34 1.95648 -0.36704 663(v),666(v),664(v),487(v)

491(v)

129. LP ( 3)Br 34 1.95326 -0.36632 664(v),666(v),488(v),490(v)

130. LP ( 1)Br 35 1.98811 -1.14490 488(v),663(v),489(v),665(v)

664(v),487(v),494(v)

131. LP ( 2)Br 35 1.95644 -0.36621 663(v),665(v),664(v),487(v)

132. LP ( 3)Br 35 1.95296 -0.36552 664(v),665(v),489(v)

487. RY*( 1) C 31 0.01566 0.52485

488. RY*( 2) C 31 0.01434 0.53443

489. RY*( 3) C 31 0.01432 0.53092

490. RY*( 4) C 31 0.00281 1.38319

491. RY*( 5) C 31 0.00277 1.38449

492. RY*( 6) C 31 0.00103 1.57757

493. RY*( 7) C 31 0.00102 1.59167

494. RY*( 8) C 31 0.00099 1.63517

495. RY*( 9) C 31 0.00089 1.05655

496. RY*( 10) C 31 0.00008 0.96434

497. RY*( 11) C 31 0.00004 1.98241

498. RY*( 12) C 31 0.00002 0.75696

499. RY*( 13) C 31 0.00002 1.19901

500. RY*( 14) C 31 0.00000 1.20446

501. RY*( 15) C 31 0.00000 23.03285

502. RY*( 16) C 31 0.00000 2.72007

503. RY*( 17) C 31 0.00000 2.71572

504. RY*( 1)Br 32 0.00315 0.73006

505. RY*( 2)Br 32 0.00189 0.62197

506. RY*( 3)Br 32 0.00183 0.59634

507. RY*( 4)Br 32 0.00074 1.22929

508. RY*( 5)Br 32 0.00053 0.86661

509. RY*( 6)Br 32 0.00048 0.81073

510. RY*( 7)Br 32 0.00030 0.54663

511. RY*( 8)Br 32 0.00023 0.45772

512. RY*( 9)Br 32 0.00019 0.55836

513. RY*( 10)Br 32 0.00014 0.64578

514. RY*( 11)Br 32 0.00007 0.78465

S74
515. RY*( 12)Br 32 0.00005 1.50851

516. RY*( 13)Br 32 0.00002 2.79745

517. RY*( 14)Br 32 0.00002 1.23909

518. RY*( 15)Br 32 0.00000 285.91970

519. RY*( 16)Br 32 0.00000 981.07053

520. RY*( 17)Br 32 0.00000 12.52445

521. RY*( 18)Br 32 0.00001 1.96696

522. RY*( 19)Br 32 0.00000 12.18862

523. RY*( 20)Br 32 0.00000 285.91365

524. RY*( 21)Br 32 0.00000 286.01258

525. RY*( 22)Br 32 0.00000 4.26598

526. RY*( 23)Br 32 0.00000 10.20404

527. RY*( 24)Br 32 0.00000 4.22651

528. RY*( 25)Br 32 0.00000 83.02813

529. RY*( 26)Br 32 0.00000 4.24573

530. RY*( 27)Br 32 0.00001 2.01291

531. RY*( 28)Br 32 0.00000 4.36893

532. RY*( 29)Br 32 0.00000 12.18268

533. RY*( 30)Br 32 0.00000 4.26855

534. RY*( 1)Br 33 0.00213 0.67668

535. RY*( 2)Br 33 0.00177 0.56722

536. RY*( 3)Br 33 0.00170 0.58176

537. RY*( 4)Br 33 0.00049 0.79204

538. RY*( 5)Br 33 0.00044 0.88884

539. RY*( 6)Br 33 0.00025 0.36108

540. RY*( 7)Br 33 0.00020 1.20858

541. RY*( 8)Br 33 0.00006 0.66609

542. RY*( 9)Br 33 0.00004 0.75565

543. RY*( 10)Br 33 0.00003 1.38354

544. RY*( 11)Br 33 0.00001 0.79824

545. RY*( 12)Br 33 0.00000 75.29295

546. RY*( 13)Br 33 0.00000 1.83982

547. RY*( 14)Br 33 0.00000 12.49712

548. RY*( 15)Br 33 0.00000 285.63320

549. RY*( 16)Br 33 0.00000 285.69346

550. RY*( 17)Br 33 0.00000 14.42450

551. RY*( 18)Br 33 0.00000 1.72714

S75
552. RY*( 19)Br 33 0.00000 12.61026

553. RY*( 20)Br 33 0.00000 285.61789

554. RY*( 21)Br 33 0.00000 1.69070

555. RY*( 22)Br 33 0.00000 4.25752

556. RY*( 23)Br 33 0.00001 0.73176

557. RY*( 24)Br 33 0.00000 4.25790

558. RY*( 25)Br 33 0.00000 12.03754

559. RY*( 26)Br 33 0.00000 4.36531

560. RY*( 27)Br 33 0.00001 0.79828

561. RY*( 28)Br 33 0.00000 4.25488

562. RY*( 29)Br 33 0.00000 985.49235

563. RY*( 30)Br 33 0.00000 4.26473

564. RY*( 1)Br 34 0.00214 0.67940

565. RY*( 2)Br 34 0.00173 0.58471

566. RY*( 3)Br 34 0.00171 0.58344

567. RY*( 4)Br 34 0.00048 0.83993

568. RY*( 5)Br 34 0.00044 0.85707

569. RY*( 6)Br 34 0.00020 1.20272

570. RY*( 7)Br 34 0.00005 0.75412

571. RY*( 8)Br 34 0.00005 0.67604

572. RY*( 9)Br 34 0.00005 0.91731

573. RY*( 10)Br 34 0.00001 0.91659

574. RY*( 11)Br 34 0.00000 12.95908

575. RY*( 12)Br 34 0.00000 76.37939

576. RY*( 13)Br 34 0.00000 1.77098

577. RY*( 14)Br 34 0.00000 12.37407

578. RY*( 15)Br 34 0.00000 285.69271

579. RY*( 16)Br 34 0.00000 984.63585

580. RY*( 17)Br 34 0.00001 0.63820

581. RY*( 18)Br 34 0.00000 1.67662

582. RY*( 19)Br 34 0.00000 12.65817

583. RY*( 20)Br 34 0.00000 285.67929

584. RY*( 21)Br 34 0.00001 1.47411

585. RY*( 22)Br 34 0.00000 4.25451

586. RY*( 23)Br 34 0.00000 285.66449

587. RY*( 24)Br 34 0.00000 4.27635

588. RY*( 25)Br 34 0.00000 1.86730

S76
589. RY*( 26)Br 34 0.00000 4.32230

590. RY*( 27)Br 34 0.00001 0.77620

591. RY*( 28)Br 34 0.00000 4.24417

592. RY*( 29)Br 34 0.00000 12.49926

593. RY*( 30)Br 34 0.00000 4.31195

594. RY*( 1)Br 35 0.00217 0.69127

595. RY*( 2)Br 35 0.00173 0.58944

596. RY*( 3)Br 35 0.00170 0.58094

597. RY*( 4)Br 35 0.00045 0.89378

598. RY*( 5)Br 35 0.00045 0.83696

599. RY*( 6)Br 35 0.00020 1.20980

600. RY*( 7)Br 35 0.00004 0.99533

601. RY*( 8)Br 35 0.00004 0.96174

602. RY*( 9)Br 35 0.00003 0.47317

603. RY*( 10)Br 35 0.00003 1.37770

604. RY*( 11)Br 35 0.00000 14.05231

605. RY*( 12)Br 35 0.00000 1.46630

606. RY*( 13)Br 35 0.00000 75.54633

607. RY*( 14)Br 35 0.00000 12.53442

608. RY*( 15)Br 35 0.00000 285.71418

609. RY*( 16)Br 35 0.00000 985.37393

610. RY*( 17)Br 35 0.00001 0.64128

611. RY*( 18)Br 35 0.00000 1.80224

612. RY*( 19)Br 35 0.00000 12.11521

613. RY*( 20)Br 35 0.00000 285.63667

614. RY*( 21)Br 35 0.00001 0.92852

615. RY*( 22)Br 35 0.00000 4.34580

616. RY*( 23)Br 35 0.00001 0.74440

617. RY*( 24)Br 35 0.00000 4.25276

618. RY*( 25)Br 35 0.00000 1.63215

619. RY*( 26)Br 35 0.00000 4.22679

620. RY*( 27)Br 35 0.00000 12.33529

621. RY*( 28)Br 35 0.00000 4.24708

622. RY*( 29)Br 35 0.00000 285.65048

623. RY*( 30)Br 35 0.00000 4.25348

663. BD*( 1) C 31 -Br 32 0.09814 0.06643

664. BD*( 1) C 31 -Br 33 0.10292 0.04269 665(g),666(g),534(g),663(g)

S77
 665. BD*( 1) C 31 -Br 34 0.10207 0.04440 666(g),664(g),564(g),663(g)

569(g)

666. BD*( 1) C 31 -Br 35 0.10208 0.04475 665(g),664(g),594(g),663(g)

599(g)

-------------------------------

Total Lewis 145.52489 ( 99.6646%)

Valence non-Lewis 0.40521 ( 0.2775%)

Rydberg non-Lewis 0.08454 ( 0.0579%)

-------------------------------

Total unit 2 146.01464 (100.0000%)

Charge unit 2 -0.01464

Characterization data

(E)-1-(2-Hydroxyphenyl)-3-phenylprop-2-en-1-one (1a):8 Rf = 0.50 (hexane/ethyl acetate

19:1); yellow solid; yield 85% (139 mg). 1H NMR (400 MHz, CDCl3) δ

12.82 (s, 1H), 7.95 (d, J = 3.2 Hz, 1H), 7.92 (d, J = 3.6 Hz, 1H), 7.72 –

7.62 (m, 3H), 7.51 (dd, J = 8.0, 7.2 Hz, 1H), 7.46 – 7.42 (m, 3H), 7.04

(d, J = 8.4 Hz, 1H), 6.96 (t, J = 7.6 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.9, 163.8,

145.6, 136.5, 134.7, 131.1, 129.8, 129.2, 128.8, 120.3, 120.2, 118.9, 118.8.

(E)-1-(2-Hydroxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-one (1b):9 Rf = 0.30 (hexane/ethyl

acetate 9:1); yellow solid; yield 76% (150 mg). 1H NMR (400 MHz, CDCl3) δ 12.55 (s, 1H),

8.28 (d, J = 15.2 Hz, 1H), 8.09 (dd, J = 8.0, 0.8 Hz, 1H), 7.89 (dd, J =

8.0, 1.2 Hz, 1H), 7.77 – 7.74 (m, 1H), 7.71 (t, J = 7.2 Hz, 1H), 7.62 –

7.56 (m, 1H), 7.55 – 7.52 (m, 1H), 7.51 – 7.47 (m, 1H), 7.04 (dd, J =

8.0, 0.8 Hz, 1H), 6.99 – 6.91 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.3, 163.8, 148.8,

140.8, 136.9, 133.7, 131.2, 130.8, 130.0, 129.4, 125.3, 125.2, 119.8, 119.2, 118.9.

S78
(E)-3-(2-Fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1c):1 Rf = 0.35 (pure

hexane); yellow solid; yield 90% (160 mg); 1H NMR (400 MHz, CDCl3) δ 12.76 (s, 1H), 8.00

(d, J = 15.6 Hz, 1H), 7.92 (dd, J = 8.0, 1.2 Hz, 1H), 7.79 (d, J = 15.6

Hz, 1H), 7.66 (td, J = 7.6, 1.6 Hz, 1H), 7.55 – 7.47 (m, 1H), 7.44 – 7.38

(m, 1H), 7.22 (t, J = 7.6 Hz, 1H), 7.18 – 7.13 (m, 1H), 7.04 (d, J = 8.4

Hz, 1H), 6.96 (t, J = 7.6 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.9, 163.8, 162.1 (d,

J = 254.9 Hz), 138.4, 136.7, 132.4 (d, J = 8.8 Hz), 130.4, 129.9, 124.8, 124.7, 123.1 (d, J = 8.1

Hz), 122.9, 120.1, 118.9 (d, J = 26.7 Hz), 116.6 (d, J = 21.9 Hz).

(E)-3-(3-Chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1d):1 Rf = 0.35 (pure

hexane); yellow solid; yield 92% (174 mg). 1H NMR (400 MHz,

CDCl3) δ 12.71 (s, 1H), 7.90 (dd, J = 8.0, 1.2 Hz, 1H), 7.82 (d, J =

15.6 Hz, 1H), 7.66 – 7.60 (m, 2H), 7.53 – 7.47 (m, 2H), 7.42 – 7.37

(m, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.05 – 7.00 (m, 1H), 6.98 – 6.92 (m, 1H); 13C{1H} NMR

(100 MHz, CDCl3) δ 193.5, 163.8, 143.8, 136.8, 136.5, 135.2, 130.8, 130.4, 129.8, 128.2,

127.1, 121.6, 120.0, 119.1, 118.8.

(E)-3-(3-Bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1e):8 Rf = 0.50 (hexane/ethyl

acetate 19:1); yellow solid; yield 70% (158 mg). 1H NMR (400

MHz, CDCl3) δ 12.70 (s, 1H), 7.91 (dd, J = 8.0, 1.6 Hz, 1H), 7.84

– 7.78 (m, 2H), 7.62 (d, J = 15.6 Hz, 1H), 7.57 – 7.53 (m, 2H), 7.53

– 7.48 (m, 1H), 7.30 (t, J = 8.0 Hz, 1H), 7.03 (dd, J = 8.4, 1.2 Hz, 1H), 6.97 – 6.93 (m, 1H);

C{1H} NMR (100 MHz, CDCl3) δ 193.5, 163.8, 143.7, 136.8, 136.8, 133.7, 131.1, 130.7,
13

129.8, 127.6, 123.3, 121.6, 120.0, 119.1, 118.8.

S79
(E)-1-(2-Hydroxyphenyl)-3-(4-isopropylphenyl)prop-2-en-1-one (1f):10 Rf = 0.45 (pure

hexane); yellow solid; yield 75% (146 mg). 1H NMR (400 MHz, CDCl3) δ 12.88 (s, 1H), 7.95

– 7.90 (m, 2H), 7.65 – 7.62 (m, 1H), 7.61 – 7.59 (m, 2H), 7.52

– 7.47 (m, 1H), 7.30 (d, J = 8.4 Hz, 2H), 7.03 (dd, J = 8.4, 1.2

Hz, 1H), 6.98 – 6.91 (m, 1H), 3.00 – 2.92 (m, 1H), 1.29 (s, 3H),

1.28 (s, 3H); 13

C{1H} NMR (100 MHz, CDCl3) δ 193.9, 163.7, 152.6, 145.7, 136.4, 132.4,

129.8, 129.0, 127.3, 120.2, 119.3, 118.9, 118.8, 34.3, 23.9 (×2).

(E)-1-(2-Hydroxyphenyl)-3-(p-tolyl)prop-2-en-1-one (1g):8 Rf = 0.45 (pure hexane); yellow

solid; yield 88% (154 mg). 1H NMR (400 MHz, CDCl3) δ 12.87

(s, 1H), 7.92 – 7.90 (m, 1H), 7.88 (d, J = 8.4 Hz, 1H), 7.60 (d, J

= 15.2 Hz, 1H), 7.55 (d, J = 8.0 Hz, 2H), 7.50 – 7.45 (m, 1H),

7.25 – 7.20 (m, 2H), 7.03 – 7.00 (m, 1H), 6.96 – 6.89 (m, 1H), 2.39 (s, 3H); 13C{1H} NMR

(100 MHz, CDCl3) δ 193.9, 163.7, 145.7, 141.7, 136.4, 132.0, 129.9, 129.7, 128.8, 120.2,

119.1, 118.9, 118.7, 21.7.

(E)-3-(4-Bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1h):8 Rf = 0.25 (pure

hexane); yellow solid; yield 92% (205 mg). 1H NMR (400 MHz,

CDCl3) δ 12.76 (s, 1H), 7.91 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 15.6

Hz, 1H), 7.64 (d, J = 15.6 Hz, 1H), 7.57 (d, J = 8.4 Hz, 2H), 7.53

(s, 1H), 7.50 (d, J = 8.0 Hz, 2H), 7.04 (d, J = 8.4 Hz, 1H), 6.95 (t, J = 7.6 Hz, 1H); 13C{1H}

NMR (100 MHz, CDCl3) δ 193.6, 163.8, 144.1, 136.7, 133.6, 132.4, 130.1, 129.8, 125.4, 120.8,

120.0, 119.1, 118.8.

S80
(E)-3-(4-Ethylphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1i):11 Rf = 0.45 (hexane/ethyl

acetate 19:1); yellow solid; yield 86% (159 mg). 1H NMR (400 MHz, CDCl3) δ 12.89 (s, 1H),

7.93 – 7.89 (m, 1H), 7.90 – 7.87 (m, 1H), 7.61 (d, J = 15.6 Hz, 1H),

7.59 – 7.56 (m, 2H), 7.49 – 7.44 (m, 1H), 7.26 (s, 1H), 7.24 (s, 1H),

7.02 (dd, J = 8.4, 1.2 Hz, 1H), 6.95 – 6.89 (m, 1H), 2.68 (q, J = 7.6

Hz, 2H), 1.25 (t, J = 7.6 Hz, 3H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.9, 163.7, 147.9,

145.7, 136.4, 132.2, 129.7, 128.9, 128.7, 120.2, 119.2, 118.9, 118.7, 28.9, 15.4.

(E)-1-(2-Hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one (1j):8 Rf = 0.60 (hexane/ethyl

acetate 19:1); yellow solid; yield 88% (149 mg); 1H NMR (400 MHz, CDCl3) δ 12.85 (s, 1H),

8.05 (d, J = 15.2 Hz, 1H), 7.88 (dd, J = 8.0, 1.2 Hz, 1H), 7.52 – 7.46 (m,

2H), 7.44 (d, J = 15.2 Hz, 1H), 7.40 (d, J = 3.6 Hz, 1H), 7.13 – 7.09 (m,

1H), 7.06 – 6.99 (m, 1H), 6.99 – 6.92 (m, 1H); 13

C{1H} NMR (100

MHz, CDCl3) δ 193.3, 163.7, 140.3, 137.9, 136.5, 132.9, 129.7, 128.7, 120.1, 118.9, 118.8.

(E)-1-(2-Hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one (1k):8 Rf = 0.40 (pure

hexane); white solid; yield 89% (178 mg). 1H NMR (400 MHz, CDCl3) δ 12.87 (s, 1H), 8.79

(d, J = 15.2 Hz, 1H), 8.28 (d, J = 8.4 Hz, 1H), 7.99 – 7.94 (m, 2H),

7.93 – 7.89 (m, 2H), 7.75 (d, J = 15.2 Hz, 1H), 7.64 – 7.59 (m, 1H),

7.58 – 7.54 (m, 2H), 7.54 – 7.49 (m, 1H), 7.07 (dd, J = 8.4, 1.2 Hz,

1H), 7.00 – 6.92 (m,1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.7, 163.9, 142.5, 136.6, 133.9,

132.2, 131.9, 131.4, 129.9, 128.9, 127.3, 126.6, 125.6, 125.5, 123.6, 122.9, 120.2, 119.1, 118.8.

S81
(E)-1-(3,5-Dichloro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1l): Rf = 0.65

(hexane/ethyl acetate 19:1); yellow solid; yield 76% (217 mg); mp 147−149 °C. 1H NMR (400

MHz, CDCl3) δ 13.36 (s, 1H), 7.98 (d, J = 15.6 Hz, 1H), 7.80 (d, J

= 2.4 Hz, 1H), 7.68 (dd, J = 7.2, 2.0 Hz, 2H), 7.58 (d, J = 2.4 Hz,

1H), 7.54 (d, J = 15.6 Hz, 1H), 7.49 – 7.40 (m, 3H); 13C{1H} NMR

(100 MHz, CDCl3) δ 192.6, 157.9, 147.6, 135.8, 134.1, 131.6, 129.2, 129.0, 127.4, 124.2,

123.3, 121.0, 118.9; IR (KBr) ~ = 3071, 2754, 1635, 1562, 1436, 1330, 1201, 1164, 773 cm-
1
; HR-MS (ESI-TOF) m/z calcd for C15H9O2Cl2 [M - H]+ 290.9979, found 290.9979.

(E)-1-(3-Bromo-5-chloro-2-hydroxyphenyl)-3-phenylprop-2-en-1-one (1m): Rf = 0.70

(hexane/ethyl acetate 19:1); yellow solid; yield 82% (222 mg); mp 128−130 °C. 1H NMR (400

MHz, CDCl3) δ 13.49 (s, 1H), 7.99 (d, J = 15.6 Hz, 1H), 7.86 (d, J

= 2.4 Hz, 1H), 7.75 (d, J = 2.4 Hz, 1H), 7.69 (dd, J = 6.8, 2.4 Hz,

2H), 7.55 (d, J = 15.6 Hz, 1H), 7.50 – 7.42 (m, 3H); 13C{1H} NMR

(100 MHz, CDCl3) δ 192.6, 158.9, 147.8, 138.9, 134.2, 131.8, 129.3, 129.1, 128.3, 123.9,

121.0, 118.9, 113.2; IR (KBr) ~ = 3066, 2921, 1636, 1562, 1430, 1328, 1207, 1157, 719 cm-
1
; HR-MS (ESI-TOF) m/z calcd for C15H9BrClO2 [M - H]+ 334.9474, found 334.9470.

(E)-1-(2-Aminophenyl)-3-phenylprop-2-en-1-one (3a):12 Rf = 0.45 (hexane/ethyl acetate

9:1); yellow solid; yield 93% (154 mg). 1H NMR (400 MHz, CDCl3) δ

7.87 (dd, J = 8.4, 1.2 Hz, 1H), 7.75 (d, J = 15.6 Hz, 1H), 7.67 – 7.63

(m, 2H), 7.60 (s, 1H), 7.45 – 7.38 (m, 3H), 7.32 – 7.27 (m, 1H), 6.73 –

6.67 (m, 2H), 6.34 (s, 2H); 13

C{1H} NMR (100 MHz, CDCl3) δ 191.8, 151.1, 143.1, 135.4,

134.4, 131.2, 130.2, 129.0, 128.4, 123.3, 119.2, 117.4, 116.0.

S82
(E)-1-(2-Aminophenyl)-3-(2-bromophenyl)prop-2-en-1-one (3b):13 Rf = 0.50 (hexane/ethyl

acetate 4:1); yellow solid; yield 86% (192 mg); 1H NMR (400 MHz, CDCl3) δ 8.07 (d, J =

15.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.72 (dd, J = 8.0, 1.2 Hz, 1H),

7.64 (d, J = 8.0 Hz, 1H), 7.53 (d, J = 15.6 Hz, 1H), 7.35 (t, J = 7.6 Hz,

1H), 7.32 – 7.27 (m, 1H), 7.26 – 7.20 (m, 1H), 6.69 (t, J = 8.0 Hz, 2H),

6.37 (s, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 191.5, 151.3, 141.4, 135.6, 134.6, 133.6,

131.3, 131.1, 127.9, 127.8, 126.2, 125.8, 118.9, 117.5, 116.0.

(E)-1-(2-Aminophenyl)-3-(o-tolyl)prop-2-en-1-one (3c):13 Rf = 0.50 (hexane/ethyl acetate

9:1); yellow solid; yield 81% (142 mg). 1H NMR (400 MHz, CDCl3) δ 8.04 (d, J = 15.6 Hz,

1H), 7.87 (dd, J = 8.4, 1.2 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.54 (d, J

= 15.6 Hz, 1H), 7.32 – 7.27 (m, 2H), 7.26 – 7.20 (m, 2H), 6.73 – 6.66

(m, 2H), 6.35 (s, 2H), 2.49 (s, 3H); 13C{1H} NMR (100 MHz, CDCl3) δ

191.8, 151.2, 140.7, 138.1, 134.4, 131.2, 130.9, 129.9, 126.5, 126.4, 124.4, 119.2, 117.4, 116.0,

20.0.

(E)-1-(2-Aminophenyl)-3-(3-chlorophenyl)prop-2-en-1-one (3d):14 Rf = 0.50 (hexane/ethyl

acetate 9:1); yellow solid; yield 73% (140 mg) ); 1H NMR (400 MHz, CDCl3) δ 7.85 (d, J =

8.0 Hz, 1H), 7.61 (t, J = 11.2 Hz, 3H), 7.48 (d, J = 5.6 Hz, 1H), 7.39 –
13
7.27 (m, 3H), 6.70 (d, J = 7.6 Hz, 2H), 6.37 (s, 2H); C{1H} NMR

(100 MHz, CDCl3) δ 191.3, 151.3, 141.3, 137.3, 135.0, 134.7, 131.1,

130.3, 130.0, 127.8, 126.7, 124.5, 118.9, 117.5, 116.1; IR (KBr) ~ = 3384, 3287, 1646, 1575,

1481, 1314, 1202, 1155, 1009, 994, 854, 762 cm-1; HR-MS (ESI-TOF) m/z calcd for

C15H12ClNONa [M + Na]+ 280.0500, found 280.0484.

S83
(E)-1-(2-Aminophenyl)-3-(p-tolyl)prop-2-en-1-one (3e):13 Rf = 0.50 (hexane/ethyl acetate

9:1); yellow solid; yield 90% (159 mg). 1H NMR (400 MHz, CDCl3) δ 7.87 (dd, J = 8.4, 1.6

Hz, 1H), 7.73 (d, J = 15.6 Hz, 1H), 7.60 (s, 1H), 7.58 – 7.50 (m,

2H), 7.32 – 7.26 (m, 1H), 7.22 (d, J = 8.0 Hz, 2H), 6.72 – 6.68 (m,

2H), 6.32 (s, 2H), 2.39 (s, 3H); 13C{1H} NMR (100 MHz, CDCl3)

δ 191.9, 151.1, 143.2, 140.7, 134.3, 132.7, 131.1, 129.8, 128.4, 122.3, 119.3, 117.4, 115.9,

21.6.

(E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one (3f):13 Rf = 0.50 (hexane/ethyl

acetate 4:1); yellow solid; yield 85% (162 mg). 1H NMR (400 MHz, CDCl3) δ 7.84 (d, J = 8.0

Hz, 1H), 7.68 (d, J = 15.6 Hz, 1H), 7.61 – 7.50 (m, 3H), 7.38 (d, J

= 8.0 Hz, 2H), 7.29 (dd, J = 14.8, 7.2 Hz, 1H), 6.70 (d, J = 6.0 Hz,

2H), 6.36 (s, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 191.4, 151.2,

141.5, 136.0, 134.6, 133.9, 131.1, 129.5, 129.3, 123.6, 118.9, 117.6, 116.0; IR (KBr) ~ = 3470,

3323, 2923, 1641, 1566, 1490, 1310, 1208, 1155, 1027, 980, 862, 778 cm-1; HR-MS (ESI-

TOF) m/z calcd for C15H12ClNONa [M + Na]+ 280.0500, found 280.0498.

(E)-1-(2-Aminophenyl)-3-(4-nitrophenyl)prop-2-en-1-one (3g):15 Rf = 0.45 (hexane/ethyl

acetate 9:1); yellow solid; yield 82% (176 mg). 1H NMR (400 MHz, CDCl3) δ 8.26 (d, J = 8.4

Hz, 2H), 7.86 – 7.81 (m, 1H), 7.75 (d, J = 8.4 Hz, 2H), 7.72 (s.

2H), 7.36 – 7.28 (m, 1H), 6.73 – 6.67 (m, 2H), 6.41 (s, 2H);
13
C{1H} NMR (100 MHz, CDCl3) δ 190.7, 151.5, 148.4, 141.7,

139.8, 135.0, 131.1, 128.8, 127.2, 124.3, 118.6, 117.6, 116.1.

S84
(E)-1-(2-Aminophenyl)-3-(4-isopropylphenyl)prop-2-en-1-one (3h):14 Rf = 0.50

(hexane/ethyl acetate 19:1); yellow solid; yield 68% (114 mg). 1H NMR (400 MHz, CDCl3) δ

7.84 (dd, J = 8.4, 1.2 Hz, 1H), 7.72 (d, J = 15.6 Hz, 1H), 7.58 (s,

1H), 7.56 – 7.52 (m, 2H), 7.29 – 7.26 (m, 1H), 7.25 – 7.21 (m,

2H), 6.71 – 6.65 (m, 2H), 6.31 (s, 2H), 2.97 – 2.86 (m, 1H), 1.26

(s, 3H), 1.24 (s, 3H); 13C{1H} NMR (100 MHz, CDCl3) δ 191.9, 151.5, 151.1, 143.1, 134.3,

133.0, 131.1, 128.5, 127.1, 122.3, 119.3, 117.4, 115.9, 34.2, 23.9 (×2).

(E)-1-(2-Aminophenyl)-3-mesitylprop-2-en-1-one (3i): Rf = 0.50 (hexane/ethyl acetate 9:1);

yellow solid; yield 87% (170 mg). mp 118−120 °C; 1H NMR (400

MHz, CDCl3) δ 7.88 (d, J = 16.0 Hz, 1H), 7.77 (d, J = 8.0 Hz, 1H),

7.32 – 7.27 (m, 1H), 7.23 (d, J = 16.0 Hz, 1H), 6.94 (s, 2H), 6.72 –

6.65 (m, 2H), 6.37 (s, 2H), 2.40 (s, 6H), 2.31 (s, 3H); 13
C{1H} NMR (100 MHz, CDCl3) δ

191.9, 151.2, 141.5, 138.3, 137.1, 134.4, 132.2, 131.2, 129.3, 128.6, 119.1, 117.4, 116.0, 21.3

(×2), 21.2; IR (KBr) ~ = 3427, 3316, 2966, 2916, 1639, 1612, 1573, 1539, 1479, 1330, 1206,

1161, 1009, 980, 848, 761 cm-1; HR-MS (ESI-TOF) m/z calcd for C18H20NO [M + H]+

266.1539, found 266.1517.

(E)-1-(2-Aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one (3j):13 Rf = 0.50 (hexane/ethyl

acetate 9:1); yellow solid; yield 71% (120 mg). 1H NMR (400 MHz,

CDCl3) δ 7.88 (d, J = 15.2 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.44 (s,

1H), 7.41 – 7.36 (m, 1H), 7.32 (d, J = 3.6 Hz, 1H), 7.31 – 7.26 (m, 1H),

7.09 – 7.05 (m, 1H), 6.72 – 6.67 (m, 2H), 6.34 (s, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ

191.1, 151.1, 140.8, 135.6, 134.4, 131.5, 130.9, 128.3, 128.3, 121.9, 119.1, 117.4, 116.0.

S85
(E)-1-(2-Aminophenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one (3k):16 Rf = 0.45

(hexane/ethyl acetate 4:1); yellow solid; yield 85% (151 mg). 1H NMR (400 MHz, CDCl3 +

DMSO-d6 ) δ 8.87 (s, 1H), 7.73 (d, J = 8.0 Hz, 1H), 7.49 (q, J =

15.6 Hz, 2H), 7.19 – 7.13 (m, 1H), 7.10 (d, J = 7.6 Hz, 1H), 7.05 –

6.94 (m, 2H), 6.82 – 6.75 (m, 1H), 6.61 (d, J = 8.4 Hz, 1H), 6.56

(t, J = 7.6 Hz, 1H), 6.38 (s, 2H); 13C{1H} NMR (100 MHz, CDCl3 + DMSO-d6) δ 191.6, 157.5,

151.0, 142.9, 136.3, 134.1, 130.9, 129.7, 122.9, 119.6, 118.7, 117.5, 117.2, 115.5, 114.7.

(E)-3-([1,1'-Biphenyl]-2-yl)-1-(2-aminophenyl)prop-2-en-1-one (3l): Rf = 0.45

(hexane/ethyl acetate 19:1); yellow solid; yield 78% (173 mg). mp 90−92 °C; 1H NMR (400

MHz, CDCl3) δ 7.83 – 7.78 (m, 2H), 7.77 (d, J = 15.6 Hz, 1H), 7.52 (d,

J = 15.6 Hz, 1H), 7.48 – 7.43 (m, 4H), 7.41 – 7.38 (m, 2H), 7.38 – 7.34

(m, 2H), 7.30 – 7.27 (m, 1H), 6.72 – 6.62 (m, 2H), 6.28 (s, 2H); 13C{1H}

NMR (100 MHz, CDCl3) δ 191.8, 151.1, 143.3, 142.2, 140.3, 134.4,

133.7, 131.2, 130.8, 129.9, 129.8, 128.5, 127.7, 127.7, 127.2, 124.7, 119.1, 117.4, 115.9; IR

(KBr) ~ = 3433, 3320, 2919, 2849, 1636, 1614, 1570, 1540, 1480, 1324, 1202, 1158, 1052,

1004, 978, 860, 788 cm-1; HR-MS (ESI-TOF) m/z calcd for C21H18NO [M + H]+ 300.1383,

found 300.1396.

(E)-1-(2-Aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (3m):16 Rf = 0.40

(hexane/ethyl acetate 4:1); yellow solid; yield 81% (170 mg). 1H NMR (400 MHz, CDCl3) δ

7.86 (dd, J = 8.4, 1.6 Hz, 1H), 7.70 (d, J = 15.6 Hz, 1H), 7.47 (d,

J = 15.5 Hz, 1H), 7.31 – 7.26 (m, 1H), 7.22 (dd, J = 8.4, 2.0 Hz,

1H), 7.15 (d, J = 2.0 Hz, 1H), 6.89 (d, J = 8.4 Hz, 1H), 6.77 –

6.63 (m, 2H), 6.31 (s, 2H), 3.95 (s, 3H), 3.92 (s, 3H); 13C{1H} NMR (100 MHz, CDCl3) δ

S86
191.9, 151.2, 151.0, 149.4, 143.3, 134.2, 131.0, 128.4, 122.9, 121.2, 119.4, 117.4, 115.9, 111.3,

110.2, 56.1 (×2).

(E)-1-(2-Aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (3n):13 Rf = 0.40

(hexane/ethyl acetate 4:1); yellow solid; yield 82% (190 mg). 1H NMR (400 MHz, CDCl3) δ

7.86 (dd, J = 8.4, 1.2 Hz, 1H), 7.65 (d, J = 15.6 Hz, 1H), 7.48 (d,

J = 15.6 Hz, 1H), 7.36 – 7.26 (m, 1H), 6.85 (s, 2H), 6.73 – 6.70

(m, 1H), 6.70 – 6.67 (m, 1H), 6.32 (s, 2H), 3.92 (s, 6H), 3.90 (s,

3H); C{1H} NMR (100 MHz, CDCl3) δ 191.7, 153.6, 151.1, 143.2, 140.2, 134.4, 131.1,
13

130.9, 122.6, 119.2, 117.5, 115.9, 105.6, 61.1, 56.4.

(E)-1-(2-Aminophenyl)-3-(naphthalen-1-yl)prop-2-en-1-one (3o):13 Rf = 0.45 (hexane/ethyl

acetate 9:1); yellow solid; yield 79% (160 mg). 1H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 15.2

Hz, 1H), 8.29 (d, J = 8.4 Hz, 1H), 7.92 (d, J = 8.4 Hz, 2H), 7.88 (d,

J = 7.6 Hz, 2H), 7.71 (d, J = 15.2 Hz, 1H), 7.63 – 7.57 (m, 1H), 7.56

– 7.50 (m, 2H), 7.35 – 7.29 (m, 1H), 6.74 – 6.69 (m, 2H), 6.41 (s,

2H); C{1H} NMR (100 MHz, CDCl3) δ 191.7, 151.3, 140.1, 134.5, 133.8, 132.9, 131.9,
13

131.2, 130.5, 128.8, 126.9, 126.4, 126.0, 125.6, 125.0, 123.8, 119.1, 117.5, 116.0.

(E)-1-(2-Aminophenyl)-3-(anthracen-9-yl)prop-2-en-1-one (3p): Rf = 0.45 (hexane/ethyl

acetate 4:1); yellow solid; yield 87% (208 mg). mp 151−153 °C; 1H NMR (400 MHz, CDCl3)

δ 8.70 (d, J = 15.6 Hz, 1H), 8.46 (s, 1H), 8.36 – 8.26 (m, 2H), 8.05 –

8.01 (m, 2H), 7.82 (dd, J = 8.0, 1.2 Hz, 1H), 7.62 (d, J = 15.6 Hz,

1H), 7.55 – 7.47 (m, 4H), 7.35 – 7.27 (m, 1H), 6.75 (d, J = 8.0 Hz,

1H), 6.70 – 6.62 (m, 1H), 6.51 (s, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 191.1, 151.5, 140.1,

S87
134.7, 132.4, 131.5, 131.3, 130.9, 129.7, 128.9, 128.1, 126.4, 125.6, 125.5, 118.9, 117.5, 116.1;

IR (KBr) ~ = 3471, 3329, 3048, 1633, 1621, 1573, 1537, 1478, 1354, 1275, 1251, 1157, 1017,

982, 971, 756 cm-1; HR-MS (ESI-TOF) m/z calcd for C23H18NO [M + H]+ 324.1383, found

324.1392.

(E)-1-(2-Amino-4,5-dibromophenyl)-3-(2-bromophenyl)prop-2-en-1-one (3q): Rf = 0.50

(hexane/ethyl acetate 19:1); yellow solid; yield 84% (264 mg); mp 150−152 °C. 1H NMR (400

MHz, CDCl3) δ 8.09 (d, J = 15.6 Hz, 1H), 7.90 (d, J = 2.4 Hz, 1H), 7.75 – 7.71 (m, 1H), 7.70

(d, J = 2.4 Hz, 1H), 7.64 (dd, J = 8.0, 1.2 Hz, 1H), 7.40 (d, J = 9.6

Hz, 1H), 7.36 (d, J = 8.4 Hz, 1H), 7.27 – 7.22 (m, 1H), 6.95 (s, 2H);

C{1H} NMR (100 MHz, CDCl3) δ 189.9, 147.1, 143.2, 139.4, 135.0, 133.7, 132.9, 131.5,
13

128.0, 127.9, 126.1, 124.9, 120.5, 112.0, 106.2; IR (KBr) ~ = 3471, 3325, 2921, 1645, 1588,

1553, 1511, 1458, 1304, 1187, 968, 740 cm-1; HR-MS (ESI-TOF) m/z calcd for C15H11Br3NO

[M + H]+ 457.8385, found 457.8379.

(E)-1-(2-Amino-4,5-dimethoxyphenyl)-3-(2-bromophenyl)prop-2-en-1-one (3r): Rf = 0.45

(hexane/ethyl acetate 9:1); yellow solid; yield 88% (326 mg); mp 139−141 °C. 1H NMR (400

MHz, CDCl3) δ 8.01 (d, J = 15.6 Hz, 1H), 7.70 (d, J = 8.0 Hz, 1H), 7.62 (d, J = 8.0 Hz, 1H),

7.41 (d, J = 15.6 Hz, 1H), 7.35 (t, J = 7.6 Hz, 1H), 7.27 – 7.17

(m, 2H), 6.47 (s, 2H), 6.16 (s, 1H), 3.89 (s, 3H), 3.86 (s, 3H);

C{1H} NMR (100 MHz, CDCl3) δ 189.2, 155.8, 149.1, 140.4, 140.2, 135.7, 133.4, 130.7,
13

127.9, 127.7, 126.5, 125.5, 113.5, 110.9, 99.3, 57.0, 55.9; IR (KBr) ~ = 3440, 3308, 2919,

1632, 1575, 1528, 1394, 1255, 1230, 1151, 973 cm-1; HR-MS (ESI-TOF) m/z calcd for

C17H17BrNO3 [M + H]+ 362.0386, found 362.0379.

S88
2-Phenylchroman-4-one (2a):3 Rf = 0.45 (hexane/ethyl acetate 9:1); white solid; yield 92%

(92 mg). 1H NMR (400 MHz, CDCl3) δ 7.94 (dd, J = 8.0, 1.6 Hz, 1H), 7.55 – 7.51 (m, 1H),

7.51 – 7.45 (m, 3H), 7.44 – 7.37 (m, 2H), 7.08 – 7.06 (m, 1H), 7.06 – 7.04

(m, 1H), 5.49 (dd, J = 13.2, 2.8 Hz, 1H), 3.10 (dd, J = 16.8, 13.2 Hz, 1H),

2.90 (dd, J = 16.8, 2.8 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 192.1,

161.7, 138.9, 136.4, 129.0, 128.9, 127.2, 126.3, 121.8, 121.1, 118.8, 79.8, 44.8; HR-MS (ESI-

TOF) m/z calcd for C15H13O2 [M + H]+ 225.0910, found 225.0926.

2-(2-Nitrophenyl)chroman-4-one (2b):17 Rf = 0.45 (hexane/ethyl acetate 4:1); yellow solid;

yield 84% (84 mg); 1H NMR (400 MHz, CDCl3) δ 8.06 (dd, J = 8.0, 1.2 Hz, 1H), 8.01 (dd, J

= 8.0, 1.2 Hz, 1H), 7.97 (dd, J = 8.0, 1.6 Hz, 1H), 7.77 (td, J = 8.0, 1.2

Hz, 1H), 7.59 – 7.54 (m, 1H), 7.54 – 7.50 (m, 1H), 7.13 – 7.07 (m, 1H),

7.04 (d, J = 8.4 Hz, 1H), 6.11 (dd, J = 13.2, 2.8 Hz, 1H), 3.22 (dd, J =

16.8, 2.8 Hz, 1H), 2.95 (dd, J = 16.8, 13.2 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 190.9,

161.3, 147.5, 136.4, 134.9, 134.2, 129.5, 128.3, 127.4, 125.0, 122.3, 121.2, 118.1, 75.8, 44.6;

IR (KBr) ~ = 2920, 2850, 1686, 1645, 1602, 1579, 1519, 1474, 1462, 1357, 1303, 1221, 1117,

1063, 989, 879, 789 cm-1; HR-MS (ESI-TOF) m/z calcd for C15H12NO4 [M + H]+ 270.0761,

found 270.0763.

2-(2-Fluorophenyl)chroman-4-one (2c):18 Rf = 0.50 (hexane/ethyl acetate 19:1); yield 87%

(87 mg); 1H NMR (400 MHz, CDCl3) δ 7.97 – 7.93 (m, 1H), 7.65 (td, J = 7.6, 1.6 Hz, 1H),

7.54 – 7.48 (m, 1H), 7.40 – 7.33 (m, 1H), 7.27 – 7.21 (m, 1H), 7.14 – 7.09

(m, 1H), 7.06 (d, J = 7.6 Hz, 2H), 5.78 (dd, J = 13.2, 3.2 Hz, 1H), 3.06

(dd, J = 16.8, 13.2 Hz, 1H), 2.93 (dd, J = 16.8, 3.2 Hz, 1H); 13C{1H} NMR

(100 MHz, CDCl3) δ 191.7, 161.6, 159.7 (d, J = 247.9 Hz), 136.3, 130.4 (d, J = 8.3 Hz), 127.6

S89
(d, J = 3.2 Hz), 127.3, 126.3 (d, J = 12.9 Hz), 124.7 (d, J = 3.1 Hz), 121.9, 121.0, 118.2, 115.9

(d, J = 21.3 Hz), 73.9, 43.8; IR (KBr) ~ = 3065, 2921, 2850, 1689, 1605, 1588, 1576, 1491,

1471, 1461, 1302, 1256, 1114, 1067, 1026, 989, 802, 757 cm-1; HR-MS (ESI-TOF) m/z calcd

for C15H12FO2 [M + H]+ 243.0816, found 243.0804.

2-(3-Chlorophenyl)chroman-4-one (2d):3 Rf = 0.45 (hexane/ethyl acetate 19:1); brownish

yellow solid; yield 78% (78 mg); 1H NMR (400 MHz, CDCl3) δ 7.93 (dd, J = 8.0, 1.6 Hz, 1H),

7.57 – 7.50 (m, 2H), 7.39 – 7.31 (m, 3H), 7.10 – 7.05 (m, 2H), 5.46

(dd, J = 13.2, 3.2 Hz, 1H), 3.04 (dd, J = 16.8, 13.2 Hz, 1H), 2.89 (dd,

J = 16.8, 3.2 Hz, 1H); 13

C{1H} NMR (100 MHz, CDCl3) δ 191.5,

161.4, 140.9, 136.5, 134.9, 130.3, 129.0, 127.2, 126.5, 124.3, 122.0, 121.0, 118.2, 78.9, 44.8;

IR (KBr) ~ = 3360, 2916, 2848, 1693, 1601, 1573, 1469, 1459, 1316, 1230, 1220, 1098, 1076,

920, 808, 788 cm-1; HR-MS (ESI-TOF) m/z calcd for C15H12ClO2 [M + H]+ 259.0520, found

259.0496.

2-(3-Bromophenyl)chroman-4-one (2e):19 Rf = 0.45 (hexane/ethyl acetate 19:1); brownish

yellow solid; yield 86% (86 mg); 1H NMR (400 MHz, CDCl3) δ 7.96 – 7.90 (m, 1H), 7.68 (s,

1H), 7.57 – 7.49 (m, 2H), 7.39 (d, J = 8.0 Hz, 1H), 7.31 (t, J = 8.0 Hz,

1H), 7.08 (td, J = 7.2, 0.8 Hz, 2H), 5.45 (dd, J = 13.2, 2.0 Hz, 1H),

3.08 – 2.98 (m, 1H), 2.89 – 2.86 (m, 1H); 13C{1H} NMR (100 MHz,

CDCl3) δ 191.49, 161.38, 141.18, 136.48, 131.97, 130.57, 129.40, 127.26, 124.77, 123.10,

122.04, 121.04, 118.25, 78.85, 44.81; IR (KBr) ~ = 3360, 3065, 2916, 2848, 1680, 1600, 1572,

1469, 1458, 1316, 1297, 1220, 1111, 1065, 915, 806, 786 cm-1; HR-MS (ESI-TOF) m/z calcd

for C15H1281BrO2 [M + H]+ 304.9995, found 304.9983.

S90
2-(4-Isopropylphenyl)chroman-4-one (2f):17 Rf = 0.50 (hexane/ethyl acetate 19:1); yellow

solid; yield 72% (72 mg); 1H NMR (400 MHz, CDCl3) δ 7.94 (dd, J = 8.0, 1.6 Hz, 1H), 7.53 –

7.48 (m, 1H), 7.42 (d, J = 8.0 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H),

7.07 – 7.03 (m, 2H), 5.46 (dd, J = 13.2, 2.8 Hz, 1H), 3.12 (dd, J =

16.8, 13.2 Hz, 1H), 2.96 (dd, J = 13.6, 6.8 Hz, 1H), 2.89 (dd, J =
13
16.8, 2.8 Hz, 1H), 1.28 (d, J = 6.9 Hz, 6H); C{1H} NMR (100

MHz, CDCl3) δ 192.3, 161.8, 149.8, 136.3, 136.2, 127.2, 127.1, 126.4, 121.7, 121.1, 118.3,

79.7, 44.6, 34.1, 24.1; IR (KBr) ~ = 2958, 2869, 1687, 1646, 1603, 1514, 1462, 1420, 1338,

1301, 1223, 1113, 1066, 1053, 906, 860, 761 cm-1; HR-MS (ESI-TOF) m/z calcd for C18H19O2

[M + H]+ 267.1380, found 267.1374.

2-(p-Tolyl)chroman-4-one (2g):3 Rf = 0.450 (hexane/ethyl acetate 19:1); yellow solid; yield

74% (74 mg); 1H NMR (400 MHz, CDCl3) δ 7.94 (dd, J = 8.0, 1.6 Hz, 1H), 7.54 – 7.47 (m,

1H), 7.38 (d, J = 8.0 Hz, 2H), 7.26 (s, 1H), 7.24 (s, 1H), 7.07 – 7.03

(m, 2H), 5.45 (dd, J = 13.2, 2.8 Hz, 1H), 3.10 (dd, J = 16.8, 13.2 Hz,
13
1H), 2.88 (dd, J = 16.8, 2.8 Hz, 1H), 2.39 (s, 3H); C{1H} NMR

(100 MHz, CDCl3) δ 192.3, 161.8, 138.9, 136.3, 135.9, 129.6, 127.2, 126.3, 121.7, 121.1,

118.3, 79.7, 44.7, 21.3; IR (KBr) ~ = 3034, 2918, 2851, 1603, 1566, 1463, 1412, 1369, 1311,

1280, 1226, 1122, 1041, 905, 815, 769 cm-1; HR-MS (ESI-TOF) m/z calcd for C16H15O2 [M +

H]+ 239.1067, found 239.1053.

2-(4-Bromophenyl)chroman-4-one (2h):3 Rf = 0.50 (hexane/ethyl acetate 19:1); yellow solid;

yield 87% (87 mg); 1H NMR (400 MHz, CDCl3) δ 7.93 (dd, J = 8.0,

1.6 Hz, 1H), 7.59 – 7.51 (m, 3H), 7.37 (d, J = 8.4 Hz, 2H), 7.09 – 7.03

(m, 2H), 5.46 (dd, J = 13.2, 2.8 Hz, 1H), 3.04 (dd, J = 16.8, 13.2 Hz,

S91
1H), 2.88 (dd, J = 16.8, 3.2 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 191.7, 161.4, 137.9,

136.5, 132.2, 127.9, 127.2, 122.9, 121.9, 121.0, 118.2, 78.9, 44.7; IR (KBr) ~ = 3357, 2916,

2847, 1686, 1596, 1488, 1460, 1320, 1298, 1221, 1111, 1065, 1025, 941, 870, 860 cm-1; HR-

MS (ESI-TOF) m/z calcd for C15H1281BrO2 [M + H]+ 304.9995, found 304.9981

2-(4-Ethylphenyl)chroman-4-one (2i):3 Rf = 0.60 (hexane/ethyl acetate 9:1); yellow solid;

yield 79% (79 mg). 1H NMR (400 MHz, CDCl3) 7.94 (dd, J = 8.0, 1.6 Hz, 1H), 7.53 – 7.48

(m, 1H), 7.41 (d, J = 8.0 Hz, 2H), 7.33 – 7.24 (m, 2H), 7.08 – 7.06 (m,

2H), 5.46 (dd, J = 13.2, 2.8 Hz, 1H), 3.11 (dd, J = 16.8, 13.2 Hz, 1H),

2.89 (dd, J = 16.8, 2.8 Hz, 1H), 2.69 (q, J = 7.6 Hz, 2H), 1.26 (t, J =

7.6 Hz, 3H); 13

C{1H} NMR (100 MHz, CDCl3) δ 192.3, 161.8, 145.2, 136.3, 136.1, 128.5,

127.2, 126.4, 121.7, 121.1, 118.3, 79.7, 44.7, 28.8, 15.7; HR-MS (ESI-TOF) m/z calcd for

C17H17O2 [M + H]+ 253.1223, found 253.1217.

2-(Thiophen-2-yl)chroman-4-one (2j):20 Rf = 0.45 (hexane/ethyl acetate 9:1); yellow solid;

yield 66% (66 mg). 1H NMR (400 MHz, CDCl3) δ 7.92 (dd, J = 8.0, 1.6 Hz, 1H), 7.53 – 7.48

(m, 1H), 7.39 – 7.35 (m, 1H), 7.15 – 7.12 (m, 1H), 7.08 – 7.05 (m, 1H),

7.05 – 7.01 (m, 2H), 5.80 – 5.74 (m, 1H), 3.20 (dd, J = 16.8, 11.6 Hz, 1H),

3.07 (dd, J = 16.8, 3.6 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 191.4,

161.0, 141.6, 136.4, 127.2, 127.0, 126.5, 126.1, 121.9, 121.1, 118.4, 75.3, 44.5; HR-MS (ESI-

TOF) m/z calcd for C13H9O2S [M - H]+ 229.0318, found 229.0298.

S92
2-(Naphthalen-1-yl)chroman-4-one (2k):20 Rf = 0.45 (hexane/ethyl acetate 19:1); white solid;

yield 77% (77 mg). 1H NMR (400 MHz, CDCl3) δ 8.08 – 8.04 (m, 1H), 8.02 (dd, J = 8.0, 1.6

Hz, 1H), 7.93 (dd, J = 6.8, 3.2 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.79

(d, J = 7.2 Hz, 1H), 7.61 – 7.50 (m, 4H), 7.13 – 7.08 (m, 2H), 6.23 (dd,

J = 13.2, 2.8 Hz, 1H), 3.27 (dd, J = 16.8, 13.2 Hz, 1H), 3.11 (dd, J =

16.8, 2.8 Hz, 1H) ); 13

C{1H} NMR (100 MHz, CDCl3) δ 192.4, 161.9, 136.4, 134.3, 134.0,

130.3, 129.5, 129.2, 127.3, 126.8, 126.1, 125.5, 124.0, 122.9, 121.9, 121.2, 118.4, 76.8, 44.1;

HR-MS (ESI-TOF) m/z calcd for C19H15O2 [M + H]+ 275.1067, found 275.1058.

6,8-Dichloro-2-phenylchroman-4-one (2l): Rf = 0.60 (hexane/ethyl acetate 19:1); yellow

solid; yield 89% (89 mg); mp 114−116 °C. 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J = 2.0 Hz,

1H), 7.58 (d, J = 2.0 Hz, 1H), 7.51 – 7.37 (m, 5H), 5.59 (dd, J = 12.0,

2.8 Hz, 1H), 3.15 – 2.97 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3)

δ 190.2, 155.8, 137.8, 135.9, 129.1, 129.1, 126.9, 126.1, 125.2, 124.4,

122.7, 80.1, 43.9; IR (KBr) ~ = 3070, 2920, 1692, 1592, 1453, 1401, 1263, 1232, 869, 755

cm-1; HR-MS (ESI-TOF) m/z calcd for C15H9O2Cl2 [M - H]+ 290.9974, found 290.9980.

8-Bromo-6-chloro-2-phenylchroman-4-one (2m): Rf = 0.65 (hexane/ethyl acetate 19:1);

yellow solid; yield 91% (91 mg); mp 116−118 °C. 1H NMR (400 MHz, CDCl3) δ 7.85 (d, J =

2.8 Hz, 1H), 7.75 (d, J = 2.8 Hz, 1H), 7.50 (dd, J = 8.0, 1.2 Hz, 2H),

7.47 – 7.42 (m, 2H), 7.42 – 7.36 (m, 1H), 5.60 (dd, J = 12.0, 3.6 Hz,

1H), 3.10 (dd, J = 17.2, 12.0 Hz, 1H), 3.02 (dd, J = 17.2, 3.6 Hz, 1H);

C{1H} NMR (100 MHz, CDCl3) δ 190.2, 156.7, 138.8, 137.9, 129.1, 129.1, 127.5, 126.0,
13

125.9, 122.5, 113.7, 80.0, 43.8; IR (KBr) ~ = 3067, 2921, 1688, 1588, 1445, 1231, 1206, 864,

748 cm-1; HR-MS (ESI-TOF) m/z calcd for C15H9BrClO2 [M - H]+ 334.9469, found 334.9470.

S93
2-Phenyl-2,3-dihydroquinolin-4(1H)-one (4a):13 Rf = 0.55 (hexane/ethyl acetate 4:1); Pale

yellow solid; yield 88% (88 mg). 1H NMR (400 MHz, CDCl3) δ 7.88 (d, J = 8.0 Hz, 1H), 7.46

(d, J = 7.2 Hz, 2H), 7.41 (t, J = 7.2 Hz, 2H), 7.38 – 7.30 (m, 2H), 6.80 (t,

J = 7.6 Hz, 1H), 6.71 (d, J = 8.0 Hz, 1H), 4.78 – 4.72 (m, 1H), 4.52 (s,

1H), 2.93 – 2.84 (m, 1H), 2.81 – 2.74 (m, 1H); 13C{1H} NMR (100 MHz,

CDCl3) δ 193.4, 151.7, 141.2, 135.5, 129.1, 128.6, 127.8, 126.8, 119.2,

118.6, 116.1, 58.7, 46.6; HR-MS (ESI-TOF) m/z calcd for C15H14NO [M + H]+ 224.1070,

found 224.1077.

2-(2-Bromophenyl)-2,3-dihydroquinolin-4(1H)-one (4b):13 Rf = 0.45 (hexane/ethyl acetate

4:1); Pale yellow solid; yield 83% (83 mg). 1H NMR (400 MHz, CDCl3) δ 7.88 (dd, J = 8.0,

1.6 Hz, 1H), 7.68 (dd, J = 8.0, 1.6 Hz, 1H), 7.59 (dd, J = 8.0, 1.2 Hz, 1H), 7.39 – 7.32 (m, 2H),

7.24 – 7.16 (m, 1H), 6.83 – 6.78 (m, 1H), 6.74 (d, J = 8.4 Hz, 1H), 5.22

(dd, J = 12.4, 4.0 Hz, 1H), 4.56 (s, 1H), 2.98 – 2.91 (m, 1H), 2.80 – 2.71

(m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 192.9, 151.6, 140.0, 135.6,

133.5, 129.8, 128.3, 127.8, 127.8, 123.1, 119.3, 118.8, 116.2, 56.9, 44.3; HR-MS (ESI-TOF)

m/z calcd for C15H1379BrNO [M + H]+ 302.0175, found 302.0162, C15H1381BrNO [M + H]+

304.0155, found 304.0153.

2-(o-Tolyl)-2,3-dihydroquinolin-4(1H)-one (4c):13 Rf = 0.45 (hexane/ethyl acetate 9:1);

yellow solid; yield 81% (81 mg). 1H NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.0 Hz, 1H), 7.65

(d, J = 7.2 Hz, 1H), 7.36 – 7.30 (m, 1H), 7.25 (dd, J = 14.8, 7.2 Hz, 2H),

7.19 (t, J = 6.8 Hz, 1H), 6.78 (t, J = 7.6 Hz, 1H), 6.72 (d, J = 8.2 Hz, 1H),

5.00 (dd, J = 13.2, 4.0 Hz, 1H), 4.48 (d, J = 12.0 Hz, 1H), 2.84 – 2.63 (m,

2H), 2.35 (s, 3H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.5, 152.1, 139.1, 135.5, 135.1, 131.0,

S94
128.1, 127.8, 126.9, 125.9, 119.0, 118.5, 116.1, 54.6, 45.3, 19.2; HR-MS (ESI-TOF) m/z calcd

for C16H16NO [M + H]+ 238.1226, found 238.1222.

2-(3-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (4d):21 Rf = 0.65 (hexane/ethyl acetate

4:1); yellow solid; yield 78% (78 mg). 1H NMR (400 MHz, CDCl3) δ 7.86 (d, J = 8.0 Hz, 1H),

7.48 (s, 1H), 7.38 – 7.30 (m, 4H), 6.81 (t, J = 7.6 Hz, 1H), 6.74 (d, J = 8.0

Hz, 1H), 4.72 (dd, J = 13.2, 2.8 Hz, 1H), 4.56 (s, 1H), 2.88 – 2.79 (m,

1H), 2.79 – 2.71 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 192.9,

151.4, 143.2, 135.7, 134.9, 130.5, 128.8, 127.7, 126.9, 124.9, 119.2,

118.9, 116.1, 58.2, 46.5; HR-MS (ESI-TOF) m/z calcd for C15H11ClNO [M - H]+ 256.0524,

found 256.0502.

2-(p-Tolyl)-2,3-dihydroquinolin-4(1H)-one (4e):13 Rf = 0.45 (hexane/ethyl acetate 9:1);

yellow solid; yield 85% (85 mg). 1H NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.0 Hz, 1H), 7.39

– 7.30 (m, 3H), 7.21 (d, J = 8.0 Hz, 2H), 6.78 (t, J = 7.6 Hz, 1H), 6.71

(d, J = 8.0 Hz, 1H), 4.70 (d, J = 13.6 Hz, 1H), 4.54 (s, 1H), 2.91 –

2.80 (m, 1H), 2.77 – 2.70 (m, 1H), 2.37 (s, 3H); 13C{1H} NMR (100

MHz, CDCl3) δ 193.6, 151.8, 138.4, 138.2, 135.5, 129.7, 127.7, 126.7, 119.1, 118.5, 116.0,

58.3, 46.6, 21.3; HR-MS (ESI-TOF) m/z calcd for C16H15NONa [M + Na]+ 260.1046, found

260.1047.

2-(4-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (4f):13 Rf = 0.45 (hexane/ethyl acetate

9:1); yellow solid; yield 84% (84 mg). 1H NMR (400 MHz, CDCl3) δ

7.86 (d, J = 8.0 Hz, 1H), 7.43 – 7.37 (m, 3H), 7.37 – 7.30 (m, 2H),

6.80 (t, J = 7.6 Hz, 1H), 6.73 (d, J = 8.0 Hz, 1H), 4.73 (dd, J = 13.2,

S95
4.0 Hz, 1H), 4.52 (s, 1H), 2.86 – 2.78 (m, 1H), 2.77 – 2.70 (m, 1H); 13C{1H} NMR (100 MHz,

CDCl3) δ 193.0, 151.5, 139.7, 135.7, 134.3, 129.3, 128.1, 127.7, 119.2, 118.8, 116.1, 58.0,

46.5; HR-MS (ESI-TOF) m/z calcd for C15H13ClNO [M + H]+ 258.0680, found 258.0660.

2-(4-Nitrophenyl)-2,3-dihydroquinolin-4(1H)-one (4g):22 Rf = 0.45 (hexane/ethyl acetate

4:1); yellow solid; yield 87% (87 mg). 1H NMR (400 MHz, CDCl3) δ 8.25 (d, J = 8.8 Hz, 2H),

7.87 (dd, J = 8.0, 1.2 Hz, 1H), 7.65 (d, J = 8.8 Hz, 2H), 7.41 – 7.35

(m, 1H), 6.87 – 6.82 (m, 1H), 6.77 (d, J = 8.0 Hz, 1H), 4.93 – 4.86

(m, 1H), 4.58 (s, 1H), 2.86 – 2.83 (m, 1H), 2.82 (s, 1H); 13
C{1H}

NMR (100 MHz, CDCl3) δ 192.1, 151.1, 148.4, 148.0, 136.1, 135.9, 127.8, 127.7, 124.5, 119.3,

116.2, 58.0, 46.3; HR-MS (ESI-TOF) m/z calcd for C15H12N2O3Na [M + Na]+ 291.0740, found

291.0738.

2-(4-Isopropylphenyl)-2,3-dihydroquinolin-4(1H)-one (4h):22 Rf = 0.50 (hexane/ethyl

acetate 19:1); yellow solid; yield 85% (85 mg). 1H NMR (400 MHz, CDCl3) δ 7.90 – 7.81 (m,

1H), 7.37 (d, J = 8.0 Hz, 2H), 7.34 – 7.29 (m, 1H), 7.26 (s, 1H),

7.25 – 7.23 (m, 1H), 6.81 – 6.74 (m, 1H), 6.68 (d, J = 8.0 Hz, 1H),

4.71 (dd, J = 13.6, 3.6 Hz, 1H), 4.51 (s, 1H), 2.97 – 2.83 (m, 2H),

2.78 – 2.72 (m, 1H), 1.27 (s, 3H), 1.25 (s, 3H); 13C{1H} NMR (100

MHz, CDCl3) δ 193.6, 151.8, 149.4, 138.5, 135.5, 127.7, 127.1, 126.8, 119.1, 118.5, 116.0,

58.3, 46.5, 34.0, 24.1 (×2) ; HR-MS (ESI-TOF) m/z calcd for C18H20NO [M + H]+ 266.1539,

found 266.1535.

S96
2-Mesityl-2,3-dihydroquinolin-4(1H)-one (4i):23 Rf = 0.50 (hexane/ethyl acetate 9:1); yellow

solid; yield 68% (68 mg). 1H NMR (400 MHz, CDCl3) δ 7.90 (dd, J

= 8.0, 1.2 Hz, 1H), 7.35 – 7.30 (m, 1H), 6.89 (s, 2H), 6.80 – 6.74 (m,

1H), 6.67 (d, J = 8.0 Hz, 1H), 5.29 – 5.21 (m, 1H), 4.37 (s, 1H), 3.31

– 3.18 (m, 1H), 2.60 – 2.54 (m, 1H), 2.48 (s, 6H), 2.28 (s, 3H); 13
C{1H} NMR (100 MHz,

CDCl3) δ 194.1, 152.1, 137.8, 137.1, 135.4, 132.5, 130.8, 128.0, 118.8, 118.1, 116.0, 54.1,

41.7, 21.4, 20.9 (×2) ; HR-MS (ESI-TOF) m/z calcd for C18H20NO [M + H]+ 266.1539, found

266.1535.

2-(Thiophen-2-yl)-2,3-dihydroquinolin-4(1H)-one (4j):13 Rf = 0.50 (hexane/ethyl acetate

9:1); yellow solid; yield 86% (86 mg). 1H NMR (400 MHz, CDCl3) δ 7.87 (dd, J = 8.0, 1.2 Hz,

1H), 7.38 – 7.31 (m, 1H), 7.30 – 7.26 (m, 1H), 7.07 (d, J = 3.2 Hz. 1H),

7.01 – 6.97 (m, 1H), 6.81 (t, J = 7.2 Hz, 1H), 6.72 (d, J = 8.0 Hz, 1H), 5.05

(dd, J = 10.8, 5.6 Hz, 1H), 4.66 (s, 1H), 2.99 – 2.93 (m, 1H), 2.92 – 2.87

(m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 192.8, 150.9, 144.7, 135.6, 127.7, 127.0, 125.3,

125.1, 119.4, 118.9, 116.1, 53.9, 47.2; HR-MS (ESI-TOF) m/z calcd for C13H12NOS [M + H]+

230.0634, found 230.0617.

2-(3-Hydroxyphenyl)-2,3-dihydroquinolin-4(1H)-one (4k): Rf = 0.45 (hexane/ethyl acetate

4:1); yellow solid; yield 76% (76 mg); mp 108−110 °C. 1H NMR (400 MHz, CDCl3 + DMSO-

d6) δ 8.49 (s, 1H), 7.35 (t, J = 8.0 Hz, 1H), 6.90 – 6.79 (m, 1H), 6.78

– 6.68 (m, 1H), 6.54 – 6.40 (m, 2H), 6.40 – 6.30 (m, 2H), 6.31 – 6.20

(m, 1H), 4.98 – 4.77 (m, 1H), 4.23 – 4.13 (m, 1H), 2.44 – 2.18 (m,

2H); 13C{1H} NMR (100 MHz, CDCl3 + DMSO-d6) δ 193.6, 157.4, 151.9, 142.5, 135.2, 129.7,

127.0, 118.3, 117.5, 117.4, 116.0, 115.3, 113.5, 57.7, 45.9; IR (KBr) ~ = 3387, 3132, 2922,

S97
2901, 2850, 1636, 1580, 1473, 1409, 1360, 1339, 1276, 1233, 1151, 1084, 994, 808, 778 cm-1;

HR-MS (ESI-TOF) m/z calcd for C15H14NO2 [M + H]+ 240.1019, found 240.1020.

2-([1,1'-Biphenyl]-2-yl)-2,3-dihydroquinolin-4(1H)-one (4l): Rf = 0.60 (hexane/ethyl acetate

4:1); white solid; yield 68% (68 mg); mp 142−143 °C. 1H NMR (400 MHz, CDCl3) δ 7.84 (d,

J = 8.0 Hz, 1H), 7.81 (d, J = 7.9 Hz, 1H), 7.49 – 7.42 (m, 1H), 7.42 – 7.34

(m, 4H), 7.31 – 7.26 (m, 3H), 7.25 (s, 1H), 6.73 (t, J = 7.6 Hz, 1H), 6.62

(d, J = 8.0 Hz, 1H), 4.89 (dd, J = 14.0, 3.6 Hz, 1H), 4.36 (s, 1H), 2.94 –

2.85 (m, 1H), 2.76 – 2.65 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.17, 151.77, 141.74,

140.35, 138.53, 135.44, 130.63, 129.08, 128.62, 128.28, 128.07, 127.71, 127.68, 126.79,

118.93, 118.40, 115.97, 54.32, 46.20; IR (KBr) ~ = 3315, 3057, 1656, 1606, 1479, 1355, 1330,

1256, 1153, 1024, 997, 757 cm-1; HR-MS (ESI-TOF) m/z calcd for C21H17NONa [M + Na]+

322.1202, found 322.1192.

2-(3,4-Dimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one (4m):21 Rf = 0.40 (hexane/ethyl

acetate 4:1); yellow solid; yield 69% (69 mg). 1H NMR (400 MHz, CDCl3) δ 7.87 (dd, J = 8.0,

1.2 Hz, 1H), 7.36 – 7.31 (m, 1H), 7.00 (s, 1H), 6.98 – 6.95(m, 1H),

6.87 (d, J = 8..0 Hz, 1H), 6.82 – 6.76 (m, 1H), 6.71 (d, J = 8.0 Hz,

1H), 4.69 (dd, J = 14.0, 3.6 Hz, 1H), 4.49 (s, 1H), 3.90 (s, 3H), 3.89

(s, 3H), 2.92 – 2.83 (m, 1H), 2.78 – 2.72 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.6,

151.7, 149.5, 149.2, 138.0, 135.5, 133.7, 127.8, 119.1, 118.6, 116.1, 111.5, 109.6, 58.5, 58.3,

56.1, 46.8; HR-MS (ESI-TOF) m/z calcd for C17H16NO3 [M - H]+ 282.1125, found 282.1120.

S98
2-(3,4,5-Trimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one (4n):13 Rf = 0.40 (hexane/ethyl

acetate 4:1); yellow solid; yield 63% (63 mg). 1H NMR (400 MHz,

CDCl3) δ 7.84 (d, J = 8.0 Hz, 1H), 7.36 – 7.31 (m, 1H), 6.77 (dd, J

= 15.6, 8.0 Hz, 2H), 6.65 (s, 2H), 4.67 (d, J = 14.0 Hz, 1H), 4.62 (s,

1H), 3.85 (s, 3H), 3.84 (s, 3H), 3.83 (s, 3H), 2.88 – 2.78 (m, 1H),

2.76 – 2.67 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.4, 153.6, 151.7, 137.8, 136.9,

135.5, 127.6, 119.1, 118.6, 116.1, 103.5, 60.9, 58.9, 56.2 (×2), 46.8; HR-MS (ESI-TOF) m/z

calcd for C18H20NO4 [M + H]+ 314.1387, found 314.1389.

2-(Naphthalen-1-yl)-2,3-dihydroquinolin-4(1H)-one (4o):24 Rf = 0.45 (hexane/ethyl acetate

9:1); yellow solid; yield 79% (79 mg). 1H NMR (400 MHz, CDCl3) δ 8.14 – 8.11 (m, 1H), 7.95

– 7.90 (m, 2H), 7.86 (d, J = 8.0 Hz, 1H), 7.80 (d, J = 7.2 Hz, 1H), 7.57

– 7.49 (m, 3H), 7.41 –7.34 (m, 1H), 6.86 – 6.81 (m, 1H), 6.77 (d, J =

8.0 Hz, 1H), 5.58 – 5.52 (m, 1H), 4.63 (s, 1H), 3.08 – 2.93 (m, 2H);

C{1H} NMR (100 MHz, CDCl3) δ 193.6, 152.0, 136.6, 135.6, 134.2, 130.5, 129.4, 129.0,
13

127.9, 126.8, 126.2, 125.7, 123.9, 122.5, 119.3, 118.7, 116.2, 54.6, 45.5; HR-MS (ESI-TOF)

m/z calcd for C19H16NO [M + H]+ 274.1226, found 274.1231.

2-(Anthracen-9-yl)-2,3-dihydroquinolin-4(1H)-one (4p): Rf = 0.60 (hexane/ethyl acetate

9:1); yellow solid; yield 81% (81 mg); mp 212−214 °C. 1H NMR (400 MHz, CDCl3) δ 9.23 (s,

1H), 8.43 (s, 1H), 8.27 (s, 1H), 8.01 (d, J = 8.0 Hz, 3H), 7.54 – 7.43 (m,

4H), 7.40 – 7.33 (m, 1H), 6.85 (t, J = 7.6 Hz, 1H), 6.72 (d, J = 8.0 Hz,

1H), 6.35 (dd, J = 15.6, 3.6 Hz, 1H), 4.80 (s, 1H), 3.80 – 3.53 (m, 1H),

2.82 – 2.71 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.8, 151.9,

135.5, 132.1, 129.8, 129.7, 129.7, 129.3, 128.2, 126.9, 125.1, 122.5, 119.1, 118.5, 116.2, 53.6,

S99
43.3; IR (KBr) ~ = 3374, 3296, 3049, 2920, 2852, 1655, 1623, 1523, 1487, 1329, 1257, 1182,

1170, 998, 790 cm-1; HR-MS (ESI-TOF) m/z calcd for C23H17NONa [M + Na]+ 346.1202,

found 346.1194.

6,7-Dibromo-2-(2-bromophenyl)-2,3-dihydroquinolin-4(1H)-one (4q): ): Rf = 0.50

(hexane/ethyl acetate 19:1); yellow solid; yield 82% (82 mg); mp 146−148 °C. 1H NMR (400

MHz, CDCl3) δ 7.96 (d, J = 2.4 Hz, 1H), 7.73 (d, J = 2.4 Hz, 1H),

7.63 (s, 1H), 7.61 (d, J = 2.0 Hz, 1H), 7.42 – 7.35 (m, 1H), 7.23 (td,

J = 7.6, 1.6 Hz, 1H), 5.23 (dd, J = 12.0, 4.0 Hz, 1H), 5.19 (s, 1H),

3.03 – 2.97 (m, 1H), 2.79 (dd, J = 16.4, 12.0 Hz, 1H); 13C{1H} NMR

(100 MHz, CDCl3) δ 190.9, 147.3, 140.1, 139.1, 133.7, 130.2, 129.7, 128.5, 127.5, 123.0,

120.9, 111.1, 110.2, 56.2, 43.1; IR (KBr) ~ = 3369, 3063, 1688, 1588, 1475, 1404, 1319, 1231,

756 cm-1; HR-MS (ESI-TOF) m/z calcd for C15H11Br3NO [M + H]+ 457.8391, found 457.8380.

2-(2-Bromophenyl)-6,7-dimethoxy-2,3-dihydroquinolin-4(1H)-one (4r): Rf = 0.40

(hexane/ethyl acetate 9:1); yellow solid; yield 84% (84 mg); mp 137−139 °C. 1H NMR (400

MHz, CDCl3) δ 7.66 (d, J = 7.6 Hz, 1H), 7.56 (dd, J = 8.0, 4.0 Hz,

1H), 7.34 (td, J = 7.6, 3.2 Hz, 1H), 7.30 (d, J = 4.4 Hz, 1H), 7.17

(td, J = 7.6, 2.4 Hz, 1H), 6.20 (s, 1H), 5.15 (dt, J = 12.8, 4.0 Hz,

1H), 4.50 (s, 1H), 3.86 (s, 3H), 3.83 (s, 3H), 2.87 (dt, J = 16.4, 4.6

Hz, 1H), 2.74 – 2.61 (m, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 191.3, 156.3, 148.4, 143.2,

140.1, 133.4, 129.7, 128.2, 127.8, 123.0, 111.7, 107.9, 98.3, 57.5, 56.2, 56.2, 43.7; IR (KBr)

~ = 3296, 1603, 1499, 1398, 1226, 1165, 750 cm-1; HR-MS (ESI-TOF) m/z calcd for

C17H17BrNO3 [M + H]+ 362.0392, found 362.0379.

S100
1-(2-Hydroxyphenyl)-3-phenylprop-2-yn-1-one (5a):2 Rf = 0.60 (hexane/ethyl acetate 4:1);

yellowish solid; yield 82% (97 mg); 1H NMR (400 MHz, CDCl3) δ 11.74 (s, 1H), 8.13 (dd, J

= 8.0, 1.6 Hz, 1H), 7.73 – 7.66 (m, 2H), 7.58 – 7.48 (m, 2H), 7.48 –

7.41 (m, 2H), 6.99 (dd, J = 12.0, 4.4 Hz, 2H); 13C{1H} NMR (100 MHz,

CDCl3) δ 182.4, 162.9, 137.3, 133.3, 133.2, 131.3, 128.9, 120.9, 119.8, 119.6, 118.3, 96.2,

85.9; HR-MS (ESI-TOF) m/z calcd for C15H11O2 [M + H]+ 223.0754, found 223.0750.

2-Phenyl-4H-chromen-4-one (5b):25 Rf = 0.55 (hexane/ethyl acetate 4:1); white solid; yield

73% (58 mg). 1H NMR (400 MHz, CDCl3 + DMSO-d6 ) δ 8.10 (d, J = 8.0 Hz, 1H), 7.84 (dd, J

= 5.2, 2.4 Hz, 2H), 7.63 (t, J = 7.6 Hz, 1H), 7.50 (d, J = 8.4 Hz, 1H), 7.44

(d, J = 5.2 Hz, 3H), 7.33 (t, J = 7.6 Hz, 1H), 6.73 (s, 1H); 13C{1H} NMR

(100 MHz, CDCl3 + DMSO-d6) δ 178.3, 163.3, 156.0, 133.7, 131.5,

131.4, 128.9, 126.1, 125.3, 125.1, 123.6, 118.0, 107.2; HR-MS (ESI-TOF) m/z calcd for

C15H11O2 [M + H]+ 223.0754, found 223.0743.

2-(4-Isopropylphenyl)chroman-4-ol (6a): Rf = 0.45 (hexane/ethyl acetate 9:1); white solid;

yield 94% (95 mg); mp 151−153 °C. 1H NMR (400 MHz, CDCl3) δ 7.49 (d, J = 7.6 Hz, 1H),

7.36 (d, J = 8.0 Hz, 2H), 7.26 – 7.23 (m, 2H), 7.20 – 7.15 (m, 1H), 6.96 (td, J = 7.6, 1.0 Hz,

1H), 6.89 – 6.84 (m, 1H), 5.13 (dd, J = 11.6, 1.6 Hz, 1H), 5.09 –

5.03 (m, 1H), 2.96 – 2.86 (m, 1H), 2.52 – 2.45 (m, 1H), 2.19 –
13
2.09 (m, 1H), 1.85 (s, 1H), 1.25 (d, J = 6.8 Hz, 6H); C{1H}

NMR (100 MHz, CDCl3) δ 154.7, 149.2, 137.9, 129.3, 127.1,

126.9, 126.3, 125.9, 121.0, 116.9, 76.9, 66.0, 39.9, 34.0, 24.1 (×2); IR (KBr) ~ = 3219, 2958,

1607, 1509, 1483, 1338, 1300, 1228, 1182, 1066, 1055, 1035, 904, 864 cm-1; HR-MS (ESI-

TOF) m/z calcd for C18H20O2Na [M + Na]+ 291.1356, found 291.1327.

S101
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S103
NMR Spectra
NMR (400 MHz, CDCl3)
1H

Figure S9. 1H NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-phenylprop-2-en-1-one (1a)

S104
NMR (100 MHz, CDCl3)
13C{1H}

Figure S10. 13C{1H} NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-phenylprop-2-en-1-one

(1a)

S105
NMR (400 MHz, CDCl3)
1H

Figure S11. 1H NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(2-nitrophenyl)prop-2-en-1-

one (1b)

S106
NMR (100 MHz, CDCl3)
13C{1H}

Figure S12. 13C{1H} NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(2-nitrophenyl)prop-2-

en-1-one (1b)

S107
 NMR (400 MHz, CDCl3)
1H

Figure S13. 1H NMR spectrum of (E)-3-(2-Fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-

one (1c)

S108
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S14. 13C{1H} NMR spectrum of (E)-3-(2-Fluorophenyl)-1-(2-hydroxyphenyl)prop-2-

en-1-one (1c)

S109
 NMR (400 MHz, CDCl3)
1H

Figure S15. 1H NMR spectrum of (E)-3-(3-Chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-

one (1d)

S110
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S16. 13C{1H} NMR spectrum of (E)-3-(3-Chlorophenyl)-1-(2-hydroxyphenyl)prop-2-

en-1-one (1d)

S111
 NMR (400 MHz, CDCl3)
1H

Figure S17. 1H NMR spectrum of (E)-3-(3-Bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-

one (1e)

S112
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S18. 13C{1H} NMR spectrum of (E)-3-(3-Bromophenyl)-1-(2-hydroxyphenyl)prop-2-

en-1-one (1e)

S113
NMR (400 MHz, CDCl3)
1H

Figure S19. 1H NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(4-isopropylphenyl)prop-2-

en-1-one (1f)

S114
NMR (100 MHz, CDCl3)
13C{1H}

Figure S20. 13C{1H} NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(4-

isopropylphenyl)prop-2-en-1-one (1f)

S115
 NMR (400 MHz, CDCl3)
1H

Figure S21. 1H NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(p-tolyl)prop-2-en-1-one (1g)

S116
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S22. 13C{1H} NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(p-tolyl)prop-2-en-1-one

(1g)

S117
 NMR (400 MHz, CDCl3)
1H

Figure S23. 1H NMR spectrum of (E)-3-(4-bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-

one (1h)

S118
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S24. 13C{1H} NMR spectrum of (E)-3-(4-bromophenyl)-1-(2-hydroxyphenyl)prop-2-

en-1-one (1h)

S119
NMR (400 MHz, CDCl3)
1H

Figure S25. 1H NMR spectrum of (E)-3-(4-Ethylphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-

one (1i)

S120
 NMR (100 MHz, CDCl3)
13C{1H}

Figure 26. 13C{1H} NMR spectrum of (E)-3-(4-Ethylphenyl)-1-(2-hydroxyphenyl)prop-2-en-

1-one (1i)

S121
NMR (400 MHz, CDCl3)
1H

Figure S27. 1H NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-

one (1j)

S122
NMR (100 MHz, CDCl3)
13C{1H}

Figure S28. 13C{1H} NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(thiophen-2-yl)prop-2-

en-1-one (1j)

S123
 NMR (400 MHz, CDCl3)
1H

Figure S29. 1H NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-

one (1k)

S124
NMR (100 MHz, CDCl3)
13C{1H}

Figure S30. 13C{1H} NMR spectrum of (E)-1-(2-Hydroxyphenyl)-3-(naphthalen-1-yl)prop-

2-en-1-one (1k)

S125
 NMR (400 MHz, CDCl3)
1H

Figure S31. 1H NMR spectrum of (E)-1-(3,5-Dichloro-2-hydroxyphenyl)-3-phenylprop-2-en-

1-one (1l)

S126
NMR (100 MHz, CDCl3)
13C{1H}

Figure S32. 13C{1H} NMR spectrum of (E)-1-(3,5-Dichloro-2-hydroxyphenyl)-3-

phenylprop-2-en-1-one (1l)

S127
NMR (400 MHz, CDCl3)
1H

Figure S33. 1H NMR spectrum of (E)-1-(3-Bromo-5-chloro-2-hydroxyphenyl)-3-

phenylprop-2-en-1-one (1m)

S128
NMR (100 MHz, CDCl3)
13C{1H}

Figure S34. 13C{1H} NMR spectrum of (E)-1-(3-Bromo-5-chloro-2-hydroxyphenyl)-3-

phenylprop-2-en-1-one (1m)

S129
 NMR (400 MHz, CDCl3)
1H

Figure S35. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-phenylprop-2-en-1-one (3a)

S130
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S36. 13C{1H} NMR spectrum (E)-1-(2-Aminophenyl)-3-phenylprop-2-en-1-one (3a)

S131
NMR (400 MHz, CDCl3)
1H

Figure S37. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(2-bromophenyl)prop-2-en-1-

one (3b)

S132
NMR (100 MHz, CDCl3)
13C{1H}

Figure S38. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(2-bromophenyl)prop-2-

en-1-one (3b)

S133
NMR (400 MHz, CDCl3)
1H

Figure S39. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(o-tolyl)prop-2-en-1-one (3c)

S134
NMR (100 MHz, CDCl3)
13C{1H}

Figure S40. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(o-tolyl)prop-2-en-1-one

(3c)

S135
NMR (400 MHz, CDCl3)
1H

Figure S41. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(3-chlorophenyl)prop-2-en-1-

one (3d)

S136
NMR (100 MHz, CDCl3)
13C{1H}

Figure S42. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(3-chlorophenyl)prop-2-

en-1-one (3d)

S137
NMR (400 MHz, CDCl3)
1H

Figure S43. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(p-tolyl)prop-2-en-1-one (3e)

S138
NMR (100 MHz, CDCl3)
13C{1H}

Figure S44. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(p-tolyl)prop-2-en-1-one

(3e)

S139
NMR (400 MHz, CDCl3)
1H

Figure S45. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-

one(3f)

S140
NMR (100 MHz, CDCl3)
13C{1H}

Figure S46. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(4-chlorophenyl)prop-2-

en-1-one(3f)

S141
 NMR (400 MHz, CDCl3)
1H

Figure S47. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(4-nitrophenyl)prop-2-en-1-one

(3g)

S142
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S48. 13C{1H} NMR spectrum of of (E)-1-(2-Aminophenyl)-3-(4-nitrophenyl)prop-2-

en-1-one (3g)

S143
NMR (400 MHz, CDCl3)
1H

Figure S49. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(4-isopropylphenyl)prop-2-en-

1-one (3h)

S144
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S50. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(4-isopropylphenyl)prop-

2-en-1-one (3h)

S145
NMR (400 MHz, CDCl3)
1H

Figure S51. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-mesitylprop-2-en-1-one (3i)

S146
NMR (100 MHz, CDCl3)
13C{1H}

Figure S52. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-mesitylprop-2-en-1-one

(3i)

S147
 NMR (400 MHz, CDCl3)
1H

Figure S53. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one

(3j)

S148
NMR (100 MHz, CDCl3)
13C{1H}

Figure S54 13C{1H} NMR spectrum of of (E)-1-(2-Aminophenyl)-3-(thiophen-2-yl)prop-2-

en-1-one (3j).

S149
 NMR (400 MHz, CDCl3 + DMSO-d6 )
1H

Figure S55. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(3-hydroxyphenyl)prop-2-en-1-

one (3k)

S150
 NMR (100 MHz, CDCl3 + DMSO-d6)
13C{1H}

Figure S56. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(3-hydroxyphenyl)prop-2-

en-1-one (3k)

S151
 NMR (400 MHz, CDCl3)
1H

Figure S57. 1H NMR spectrum of (E)-3-([1,1'-Biphenyl]-2-yl)-1-(2-aminophenyl)prop-2-en-

1-one (3l)

S152
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S58. 13C{1H} NMR spectrum of (E)-3-([1,1'-Biphenyl]-2-yl)-1-(2-aminophenyl)prop-

2-en-1-one (3l)

S153
NMR (400 MHz, CDCl3)
1H

Figure S59. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-

en-1-one (3m)

S154
NMR (100 MHz, CDCl3)
13C{1H}

Figure S60. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(3,4-

dimethoxyphenyl)prop-2-en-1-one (3m)

S155
NMR (400 MHz, CDCl3)
1H

Figure S61. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-

2-en-1-one (3n)

S156
NMR (100 MHz, CDCl3)
13C{1H}

Figure S62. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(3,4,5-

trimethoxyphenyl)prop-2-en-1-one (3n)

S157
NMR (400 MHz, CDCl3)
1H

Figure S63. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(naphthalen-1-yl)prop-2-en-1-

one (3o)

S158
NMR (100 MHz, CDCl3)
13C{1H}

Figure S64. 13C{1H} NMR spectrum of (E)-1-(2-Aminophenyl)-3-(naphthalen-1-yl)prop-2-

en-1-one (3o)

S159
NMR (400 MHz, CDCl3)
1H

Figure S65. 1H NMR spectrum of (E)-1-(2-Aminophenyl)-3-(anthracen-9-yl)prop-2-en-1-

one (3p)

S160
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S66. 13C{1H} NMR spectrum of of (E)-1-(2-Aminophenyl)-3-(anthracen-9-yl)prop-2-

en-1-one (3p)

S161
NMR (400 MHz, CDCl3)
1H

Figure S67. 1H NMR spectrum of (E)-1-(2-Amino-4,5-dibromophenyl)-3-(2-

bromophenyl)prop-2-en-1-one (3q)

S162
NMR (100 MHz, CDCl3)
13C{1H}

Figure S68. 13C{1H} NMR spectrum of (E)-1-(2-Amino-4,5-dibromophenyl)-3-(2-

bromophenyl)prop-2-en-1-one (3q)

S163
NMR (400 MHz, CDCl3)
1H

Figure S69. 1H NMR spectrum of (E)-1-(2-Amino-4,5-dimethoxyphenyl)-3-(2-

bromophenyl)prop-2-en-1-one (3r)

S164
NMR (100 MHz, CDCl3)
13C{1H}

Figure S70. 13C{1H} NMR spectrum of (E)-1-(2-Amino-4,5-dimethoxyphenyl)-3-(2-

bromophenyl)prop-2-en-1-one (3r)

S165
NMR (400 MHz, CDCl3)
1H

Figure S71. 1H NMR spectrum of 2-Phenylchroman-4-one (2a)

S166
NMR (100 MHz, CDCl3)
13C{1H}

Figure S72. 13C{1H} NMR spectrum of 2-Phenylchroman-4-one (2a)

S167
NMR (400 MHz, CDCl3)
1H

Figure S73. 1H NMR spectrum of 2-(2-Nitrophenyl)chroman-4-one (2b)

S168
NMR (100 MHz, CDCl3)
13C{1H}

Figure S74. 13C{1H} NMR spectrum of 2-(2-Nitrophenyl)chroman-4-one (2b)

S169
NMR (400 MHz, CDCl3)
1H

Figure S75. 1H NMR spectrum of 2-(2-Fluorophenyl)chroman-4-one (2c)

S170
NMR (100 MHz, CDCl3)
13C{1H}

Figure S76. 13C{1H} NMR spectrum of 2-(2-Fluorophenyl)chroman-4-one (2c)

S171
NMR (400 MHz, CDCl3)
1H

Figure S77. 1H NMR spectrum of 2-(3-Chlorophenyl)chroman-4-one (2d)

S172
NMR (100 MHz, CDCl3)
13C{1H}

Figure S78. 13C{1H} NMR spectrum of 2-(3-Chlorophenyl)chroman-4-one (2d)

S173
NMR (400 MHz, CDCl3)
1H

Figure S79. 1H NMR spectrum of 2-(3-Bromophenyl)chroman-4-one (2e)

S174
NMR (100 MHz, CDCl3)
13C{1H}

Figure S80. 13C{1H} NMR spectrum of 2-(3-Bromophenyl)chroman-4-one (2e)

S175
NMR (400 MHz, CDCl3)
1H

Figure S81. 1H NMR spectrum of 2-(4-Isopropylphenyl)chroman-4-one (2f)

S176
NMR (100 MHz, CDCl3)
13C{1H}

Figure S82. 13C{1H} NMR spectrum of 2-(4-Isopropylphenyl)chroman-4-one (2f)

S177
NMR (400 MHz, CDCl3)
1H

Figure S83. 1H NMR spectrum of 2-(p-Tolyl)chroman-4-one (2g)

S178
NMR (100 MHz, CDCl3)
13C{1H}

Figure S84. 13C{1H} NMR spectrum of 2-(p-Tolyl)chroman-4-one (2g)

S179
NMR (400 MHz, CDCl3)
1H

Figure S85. 1H NMR spectrum of 2-(4-Bromophenyl)chroman-4-one (2h)

S180
NMR (100 MHz, CDCl3)
13C{1H}

Figure S86. 13C{1H} NMR spectrum of 2-(4-Bromophenyl)chroman-4-one (2h)

S181
NMR (400 MHz, CDCl3)
1H

Figure S87. 1H NMR spectrum of 2-(4-Ethylphenyl)chroman-4-one (2i)

S182
NMR (100 MHz, CDCl3)
13C{1H}

Figure S88. 13C{1H} NMR spectrum of 2-(4-Ethylphenyl)chroman-4-one (2i)

S183
NMR (400 MHz, CDCl3)
1H

Figure S89. 1H NMR spectrum of 2-(Thiophen-2-yl)chroman-4-one (2j)

S184
NMR (100 MHz, CDCl3)
13C{1H}

Figure S90. 13C{1H} NMR spectrum of 2-(Thiophen-2-yl)chroman-4-one (2j)

S185
NMR (400 MHz, CDCl3)
1H

Figure S91. 1H NMR spectrum of 2-(Naphthalen-1-yl)chroman-4-one (2k)

S186
NMR (100 MHz, CDCl3)
13C{1H}

Figure S92. 13C{1H} NMR spectrum of 2-(Naphthalen-1-yl)chroman-4-one (2k)

S187
NMR (400 MHz, CDCl3)
1H

Figure S93. 1H NMR spectrum of 6,8-Dichloro-2-phenylchroman-4-one (2l)

S188
NMR (100 MHz, CDCl3)
13C{1H}

Figure S94. 13C{1H} NMR spectrum of 6,8-Dichloro-2-phenylchroman-4-one (2l)

S189
NMR (400 MHz, CDCl3)
1H

Figure S95. 1H NMR spectrum of 8-Bromo-6-chloro-2-phenylchroman-4-one (2m)

S190
NMR (100 MHz, CDCl3)
13C{1H}

Figure S96. 13C{1H} NMR spectrum of 8-Bromo-6-chloro-2-phenylchroman-4-one (2m)

S191
NMR (400 MHz, CDCl3)
1H

Figure S97. 1H NMR spectrum of 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (4a)

S192
NMR (100 MHz, CDCl3)
13C{1H}

Figure S98. 13C{1H} NMR spectrum of 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (4a)

S193
NMR (400 MHz, CDCl3)
1H

Figure S99. 1H NMR spectrum of 2-(2-Bromophenyl)-2,3-dihydroquinolin-4(1H)-one (4b)

S194
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S100. 13C{1H} NMR spectrum of 2-(2-Bromophenyl)-2,3-dihydroquinolin-4(1H)-one

(4b)

S195
NMR (400 MHz, CDCl3)
1H

Figure S101. 1H NMR spectrum of 2-(o-Tolyl)-2,3-dihydroquinolin-4(1H)-one (4c)

S196
NMR (100 MHz, CDCl3)
13C{1H}

Figure S102. 13C{1H} NMR spectrum of 2-(o-Tolyl)-2,3-dihydroquinolin-4(1H)-one ( 4c)

S197
 NMR (400 MHz, CDCl3)
1H

Figure S103. 1H NMR spectrum of 2-(3-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (4d)

S198
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S104. 13C{1H} NMR spectrum of2-(3-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one

(4d)

S199
NMR (400 MHz, CDCl3)
1H

Figure S105. 1H NMR spectrum of 2-(p-Tolyl)-2,3-dihydroquinolin-4(1H)-one (4e)

S200
NMR (100 MHz, CDCl3)
13C{1H}

Figure S106. 13C{1H} NMR spectrum of 2-(p-Tolyl)-2,3-dihydroquinolin-4(1H)-one (4e)

S201
NMR (400 MHz, CDCl3)
1H

Figure S107. 1H NMR spectrum of 2-(4-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (4f)

S202
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S108. 13C{1H} NMR spectrum of 2-(4-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one

(4f)

S203
NMR (400 MHz, CDCl3)
1H

Figure S109. 1H NMR spectrum of 2-(4-Nitrophenyl)-2,3-dihydroquinolin-4(1H)-one (4g)

S204
NMR (100 MHz, CDCl3)
13C{1H}

Figure S110. 13C{1H} NMR spectrum of 2-(4-Nitrophenyl)-2,3-dihydroquinolin-4(1H)-one

(4g)

S205
NMR (400 MHz, CDCl3)
1H

Figure S111. 1H NMR spectrum of 2-(4-Isopropylphenyl)-2,3-dihydroquinolin-4(1H)-one

(4h)

S206
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S112. 13C{1H} NMR spectrum of 2-(4-Isopropylphenyl)-2,3-dihydroquinolin-4(1H)-

one (4h)

S207
NMR (400 MHz, CDCl3)
1H

Figure S113. 1H NMR spectrum of 2-Mesityl-2,3-dihydroquinolin-4(1H)-one (4i)

S208
NMR (100 MHz, CDCl3)
13C{1H}

Figure S114. 13C{1H} NMR spectrum of 2-Mesityl-2,3-dihydroquinolin-4(1H)-one (4i)

S209
 NMR (400 MHz, CDCl3)
1H

Figure S115. 1H NMR spectrum of 2-(Thiophen-2-yl)-2,3-dihydroquinolin-4(1H)-one (4j)

S210
NMR (100 MHz, CDCl3)
13C{1H}

Figure S116. 13C{1H} NMR spectrum of 2-(Thiophen-2-yl)-2,3-dihydroquinolin-4(1H)-one

(4j)

S211
NMR (400 MHz, CDCl3 + DMSO-d6)
1H

Figure S117. 1H NMR spectrum of 2-(3-Hydroxyphenyl)-2,3-dihydroquinolin-4(1H)-one

(4k)

S212
NMR (100 MHz, CDCl3 + DMSO-d6)
13C{1H}

Figure S118. 13C{1H} NMR spectrum of 2-(3-Hydroxyphenyl)-2,3-dihydroquinolin-4(1H)-

one (4k)

S213
NMR (400 MHz, CDCl3)
1H

Figure S119. 1H NMR spectrum of 2-([1,1'-Biphenyl]-2-yl)-2,3-dihydroquinolin-4(1H)-one

(4l)

S214
NMR (100 MHz, CDCl3)
13C{1H}

Figure S120. 13C{1H} NMR spectrum of 2-([1,1'-Biphenyl]-2-yl)-2,3-dihydroquinolin-

4(1H)-one (4l)

S215
NMR (400 MHz, CDCl3)
1H

Figure S121. 1H NMR spectrum of 2-(3,4-Dimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-

one (4m)

S216
NMR (100 MHz, CDCl3)
13C{1H}

Figure S122. 13C{1H} NMR spectrum of 2-(3,4-Dimethoxyphenyl)-2,3-dihydroquinolin-

4(1H)-one (4m)

S217
 NMR (400 MHz, CDCl3)
1H

Figure S123. 1H NMR spectrum of 2-(3,4,5-Trimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-

one (4n)

S218
NMR (100 MHz, CDCl3)
13C{1H}

Figure S124. 13C{1H} NMR spectrum of 2-(3,4,5-Trimethoxyphenyl)-2,3-dihydroquinolin-

4(1H)-one (4n)

S219
 NMR (400 MHz, CDCl3)
1H

Figure S125. 1H NMR spectrum of 2-(Naphthalen-1-yl)-2,3-dihydroquinolin-4(1H)-one (4o)

S220
NMR (100 MHz, CDCl3)
13C{1H}

Figure S126. 13C{1H} NMR spectrum of 2-(Naphthalen-1-yl)-2,3-dihydroquinolin-4(1H)-

one (4o)

S221
NMR (400 MHz, CDCl3)
1H

Figure S127. 1H NMR spectrum of 2-(Anthracen-9-yl)-2,3-dihydroquinolin-4(1H)-one (4p)

S222
 NMR (100 MHz, CDCl3)
13C{1H}

Figure S128. 13C{1H} NMR spectrum of 2-(Anthracen-9-yl)-2,3-dihydroquinolin-4(1H)-one

(4p)

S223
NMR (400 MHz, CDCl3)
1H

Figure S129. 1H NMR spectrum of 6,7-Dibromo-2-(2-bromophenyl)-2,3-dihydroquinolin-

4(1H)-one (4q)

S224
NMR (100 MHz, CDCl3)
13C{1H}

Figure S130. 13C{1H} NMR spectrum of 6,7-Dibromo-2-(2-bromophenyl)-2,3-

dihydroquinolin-4(1H)-one (4q)

S225
 NMR (400 MHz, CDCl3)
1H

Figure S131. 1H NMR spectrum of 2-(2-Bromophenyl)-6,7-dimethoxy-2,3-dihydroquinolin-

4(1H)-one (4r)

S226
NMR (100 MHz, CDCl3)
13C{1H}

Figure S132. 13C{1H} NMR spectrum of 2-(2-Bromophenyl)-6,7-dimethoxy-2,3-

dihydroquinolin-4(1H)-one (4r)

S227
NMR (400 MHz, CDCl3)
1H

Figure S133. 1H NMR spectrum of 1-(2-Hydroxyphenyl)-3-phenylprop-2-yn-1-one (5a)

S228
NMR (100 MHz, CDCl3)
13C{1H}

Figure S134. 13C{1H} NMR spectrum of 1-(2-Hydroxyphenyl)-3-phenylprop-2-yn-1-one

(5a)

S229
NMR (400 MHz, CDCl3 + DMSO-d6 )
1H

Figure S135. 1H NMR spectrum of 2-Phenyl-4H-chromen-4-one (5b)

S230
NMR (100 MHz, CDCl3 + DMSO-d6)
13C{1H}

Figure S136. 13C{1H} NMR spectrum of 2-Phenyl-4H-chromen-4-one (5b)

S231
NMR (400 MHz, CDCl3)
1H

Figure S137. 1H NMR spectrum of 2-(4-Isopropylphenyl)chroman-4-ol (6a)

S232
NMR (100 MHz, CDCl3)
13C{1H}

Figure S138. 13C{1H} NMR spectrum of 2-(4-Isopropylphenyl)chroman-4-ol (6a)

S233
NMR (700 MHz, CDCl3)
1H

Figure S139. 1H NMR spectrum of the crude reaction mixture showing the absence of any
decomposition product of CBr4

S234
 NMR (175 MHz, CDCl3)
13C{1H}

Figure S140. 13C{1H} NMR spectrum of the crude reaction mixture showing the presence of
CBr4 and absence of any decomposition product of CBr4.

S235
Structure determination of 6a.

1H NMR (400 MHz, DMSO-d6)

Figure S141. 1H NMR spectrum of 2-(4-Isopropylphenyl)chroman-4-ol (6a) in DMSO-d6.

13C{1H} NMR (100 MHz, DMSO-d6)

Figure S142. 13C{1H} NMR spectrum of 2-(4-Isopropylphenyl)chroman-4-ol (6a) in DMSO-

d6.

S236
From the HSQC spectrum, the single bond-connected proton can be identified and well

distinguished. The two protons are resonating at a frequency of 4.97 and 5.19 ppm respectively.

From the NOESY experiment, it can be found that those two protons are within a distance of

4-5 Å. The 1D row extract was also supportive of the fact.

Figure S143. HSQC Spectra.

From the HSQC study, it was observed that the single bond connectivity of Ha (4.97) is with
C (64.4 ppm). C (79.3) also shows a single bond correlation with Hb (5.195 ppm).

S237
Figure S144. NOESY Spectra.

S238
 Figure S145. Difference-NOE 1D Spectra.

Figure S146. Possible geometry (racemic mixture) of 6a.

S239