Proceeding Paper

Computational Survey of Two Specific Chalcone Derivatives to

Study Their Structural, Electronic, and Chemical Behavior †
Rahul A. Shinde 1, Bhatu S. Desale 1, Tushar Janardan Pawar 2, Dipak B. Patil 2, Vishnu A. Adole 3,*
and Bapu S. Jagdale 3,*

1 Department of Chemistry, Mahatma Gandhi Vidyamandir´s Arts, Science and Commerce College, Manmad
(Affiliated to Savitribai Phule Pune University, Pune), Nashik 423104, Maharashtra, India; ra-
[email protected] (R.A.S.); [email protected] (B.S.D.)
2 Departamento de Química, División de Ciencias Naturales y Exactas, Campus Guanajuato,

Universidad de Guanajuato, Noria Alta S/N, Guanajuato 36050, Gto., Mexico [email protected]
(T.J.P.); [email protected] (D.B.P.)
3 Department of Chemistry, Mahatma Gandhi Vidyamandir´s Loknete Vyankatrao Hiray Arts, Science and

Commerce College, Panchavati (Affiliated to Savitribai Phule Pune University, Pune),

Nashik 422003, Maharashtra, India
* Correspondence: [email protected] (V.A.A.); [email protected] (B.S.J.)
† Presented at the 26th International Electronic Conference on Synthetic Organic Chemistry; Available online:
https://ecsoc-26.sciforum.net.

Abstract: Two previously reported 2,3-dihydro-1H-inden-1-one derived chalcone derivatives have

been studied using density functional theory (DFT). This computational approach includes struc-
tural, electronic, physical, and chemical behavior of (E)-2-(thiophen-2-ylmethylene)-2,3-dihydro-
1H-inden-1-one (TMDHI) and (E)-2-((1H-pyrrol-2-yl)methylene)-2,3-dihydro-1H-inden-1-one
(PMDHI). The geometry of compounds was optimized by employing the DFT method with the
Citation: Shinde, R.A.; Desale, B.S.;
B3LYP/6-311G (d,p) basis set. In this comparative study, various properties such as bond angle,
Pawar, T.J.; Patil, D.B.; Adole, V.A.;
bond length, dipole moment, augmentation in dipole moment, and total energy of TMDHI and
Jagdale, B.S. Computational Survey
PMDHI are revealed. Also, the study shows that the Mulliken atomic charges analysis revealed that
of Two Specific Chalcone
Derivatives to Study Their
all hydrogen atoms in both compounds have a positive charge and the molecular electrostatic sur-
Structural, Electronic, and Chemical
face potential plot of the title compounds showed negative potential located around the oxygen
Behavior. Chem. Proc. 2022, 4, x. atom.
https://doi.org/10.3390/xxxxx
Keywords: DFT; Chalcone; TMDHI; PMDHI
Academic Editor(s): Julio A. Seijas

Published: 15 November 2022

Publisher’s Note: MDPI stays neu-

tral with regard to jurisdictional
1. Introduction
claims in published maps and institu- The chemistry of chalcones is one of the popular fields of organic synthesis. The ex-
tional affiliations. ploration of Chalcones and related compounds always uncovers new methodologies and
biological properties. Also, it has been found that chalcones acquired many applications
in medicinal chemistry and biological science. [1–6] Furthermore, arylidene indanones,
Copyright: © 2022 by the authors. being one of the important chalcone skeletons commonly discovers surprising pharmaco-
Submitted for possible open access logical applications due to the presence of α,β-unsaturated enone framework. [7–9] To
publication under the terms and con- comprehend the biological activity of chemical compounds, it is important to know their
ditions of the Creative Commons At- physical and chemical properties. Theoretical computations dependent on DFT have been
tribution (CC BY) license (https://cre- effectively investigated to a great extent in the past couple of years to decide different
ativecommons.org/licenses/by/4.0/). various structural aspects of synthetically and pharmacologically vital organic motifs.
[10–12] The density functional theory (DFT) inferred theoretical quantum calculations
have been effectively utilized in many areas of science. DFT is a method that can generate
a great deal of information about the physical and chemical behavior of various molecules.
viet. [11–14] Cross-coupling reaction, equilibrium isotopic fractionation, pericyclic reac-
tion, density-viscosity studies, catalysis, and photoelectronic applications are some

Chem. Proc. 2022, 4, x. https://doi.org/10.3390/xxxxx www.mdpi.com/journal/chemproc

Chem. Proc. 2022, 4, x FOR PEER REVIEW 2 of 9

evident examples of DFT applications. [15–18] DFT calculations are useful for determining
the structure and other important properties of molecules. DFT/B3LYP method utilizing
different basis sets has been observed to be extremely crucial for researching chemical,
electronic, thermodynamic and quantum chemical parameters. Also, bond lengths, bond
angles, dipole moment, charge distribution, reactive sites, and other features could be in-
vestigated using the DFT method based on a computational study. The Computational
study can be used to perform spectroscopic examinations such as IR, UV/Visible spectra,
Raman, and NMR. In addition, DFT computations can also predict frontier molecular or-
bital energies and thereby the electronic excitation energy. [19–21] In continuation of our
previous work and by considering these essential aspects, here we present a successful
attempt to investigate structural parameters such as total energy, charge density, absolute
electronegativity (χ), softness (σ), hardness (ɳ), and electron transferred (ΔN), the electron
density in highest occupied molecular orbital (HOMO) and lowest unoccupied molecular
orbital (LUMO), of two previously synthesized arylidene indanones.

2. Methodology
2.1. Materials and Methods
The high-purity chemicals were purchased from a local distributor. The compounds
were used exactly as they were received, with no further purification required. The melt-
ing point was investigated by the uncorrected open capillary. FT-IR spectra were obtained
using potassium bromide pellets, while 1H and 13C NMR spectra were recorded with
Bruker using CDCl3 as the solvent. Thin-layer chromatography with aluminum sheets and
silica gel 60 F254 was used to monitor the reaction (Merck).

2.2. Experimental Procedure for the Synthesis of TMDHI and PMDHI

The Claisen-Schmidt condensation reaction was used to synthesize the compounds
TMDHI and PMDHI. In a typical synthesis method 2,3-dihydro-1H-inden-1-one (1, 10
mmol) and thiophene-2-carbaldehyde (2a, 10 mmol) or pyrrole-2-carbaldehyde (2b, 10
mmol) were combined in 10 mL ethyl alcohol. 5 mL 30% NaOH was added to this. The
alkaline mixture was then stirred for 5-10 min at room temperature until the result formed.
After the reaction was completed, it was poured onto crushed ice (as determined by TLC).
It was then acidified with dilute HCl, filtered, dried, and recrystallized with hot ethanol
to produce pure crystals of the products. The reaction is presented in Scheme 1.

Scheme 1. Synthesis of the TMDHI and PMDHI.

2.3. Computational Details

Density Functional Theory (DFT) calculations were performed using the Gaussian-03
program package on an Intel (R) Core (TM) i5 computer with no geometry constraints.
The DFT/B3LYP method was used to optimize the geometry of the title compounds using
the 6-311G (d,p) basis set. The Guassview 4.1 molecular visualization program was used
to create optimized geometry. The molecular electrostatic potential was computed using
the same method to study the reactive sites of the title compounds. All the computations
were done in the gas phase for the optimized structure. The DFT/B3LYP method with 6-
311G (d,p) basis set was used to calculate Mulliken atomic charges.

3. Results and Discussion

3.1. Spectral Analysis of TMDHI and PMDHI
Chem. Proc. 2022, 4, x FOR PEER REVIEW 3 of 9

3.1.1. (E)-2-(Thiophen-2-ylmethylene)-2,3-dihydro-1H-inden-1-one (3a or TMDHI,

C14H10OS)
Pale Yellow color; Yield 97%; m.p.: 122-124 °C; FT-IR (KBr, cm−1): 3059.10, 2873.94,
1672.28, 1469.76 1415.75, 1371.39, 1251.80, 1201.65, 1099.43, 1029.99, 952.84, 908.47, 831.32,
781.17, 725.23, 663.51, 524.64, 472.56, 424.34, 358.76; 1H NMR (500 MHz, CDCl3) δ 3.97–3.93
(m, 2H), 7.18 (dd, J = 5.0, 3.7 Hz, 1H), 7.47–7.40 (m, 2H), 7.61–7.55 (m, 2H), 7.66–7.61 (m,
1H), 7.92–7.87 (m, 2H); 13C NMR (126 MHz, CDCl3) δ 193.89, 149.07, 139.92, 138.56, 134.58,
133.16, 132.76, 130.57, 128.23, 126.62, 127.69, 126.26, 124.34, 32.35.

3.1.2. (E)-2-((1H-pyrrol-2-yl)methylene)-2,3-dihydro-1H-inden-1-one (3b or PMDHI,

C14H11ON)
Yellow color; Yield 85%; m.p.: 166-170 °C; FT-IR (KBr, cm−1): 3059.10, 1668.43, 1597.06,
1415.75, 1369.46, 1317.38, 1247.94, 1201.65, 1107.14, 1068.56, 1026.13, 981.77, 908.47, 827.46,
779.24, 721.38, 663.51, 520.78, 470.63, 381.91; 1H NMR (500 MHz, CDCl3) δ 9.05 (s, 1H), 7.89
(ddd, J = 7.7, 1.3, 0.7 Hz, 1H), 7.67 (m, 1H), 7.63–7.53 (m, 2H), 7.47–7.39 (m, 1H), 7.08 (m,
1H), 6.76 (s, 1H), 6.46–6.40 (m, 1H), 3.92–3.88 (m, 2H); 13C NMR (126 MHz, CDCl3) δ 194.06,
148.87, 138.94, 134.14, 129.38, 129.25, 127.56, 126.11, 124.06, 123.66, 122.91, 114.89, 111.99,
32.37.

3.2. Computational Study

3.2.1. Molecular Structure, Bond Length, Bond Angle
Figure 1 shows the optimized molecular structure of the title compounds. Due to the
overall asymmetry of the compounds, it is easy to see that both TMDHI and PMDHI have
C1 point group symmetry from optimized molecular structures. Furthermore, the
presence of a non-planar dihydrofuran ring in both compounds is evident.
Dihydrofuran’s non-planarity is due to the -CH2- group (besides the oxygen atom), which
is either above or below the plane. As a result, neither compound has a molecular plane
(h). It can also be seen that the remaining skeletons of these compounds are in an ideal
planar position, indicating that TMDHI and PMDHI have optimum geometrical
structures. The optimized molecular geometry provides a good deal of information and
therefore can have extended conjugation. This information is very much useful for the
determination of various spectroscopic entities. The optimized geometrical parameters
like bond lengths and bond angles of TMDHI and PMDHI are presented in Tables 1–4
respectively. The carbonyl bond length in TMDHI (C9-O14) and PMDHI (C1-O10) is 1.26
Å . The olefinic in both TMDHI (C10-C15) and PMDHI (C2-C11) is exactly the same 1.3552
Å . Other bond lengths are also in good agreement with the optimized structures. Bond
angle data of both compounds are also in good agreement. PMDHI (4.97 Debye) appears
to be more polar than TMDHI (4.28 Debye) based on the dipole moment data. The
augmentation in the dipole moment in PMDHI is obviously due to the presence of a more
electronegative nitrogen atom.

Figure 1. The optimized molecular structures of TMDHI and PMDHI at DFT B3LYP/6-311G(d,p)
basis set.
Chem. Proc. 2022, 4, x FOR PEER REVIEW 4 of 9

Table 1. Optimized geometrical parameters of TMDHI by DFT/B3LYP with 6-311G (d,p) basis set.

Bond Bond Length (Å) Bond Bond Length (Å)

C1-C2 1.4111 C10-C11 1.5425
C1-C6 1.4193 C10-C15 1.3552
C1-H7 1.0700 C11-C12 1.0700
C2-C3 1.3927 C11-H13 1.0700
C2-H8 1.0700 C15-H16 1.0700
C3-C4 1.3879 C15-C17 1.4014
C3-C11 1.5518 C17-C18 1.3642
C4-C5 1.3912 C17-S24 1.7639
C4-C9 1.5312 C18-C20 1.4240
C5-C6 1.4096 C18-H21 1.0700
C5-C25 1.0700 C19-C20 1.3642
C6-C26 1.0700 C19-H22 1.0700
C9-C10 1.5307 C19-S24 1.7639
C9-O14 1.2584 C20-H23 1.0700

Table 2. Optimized geometrical parameters of TMDHI by DFT/B3LYP with 6-311G(d,p) basis set.

Bond Bond Angle (°) Bond Bond Angle (°)

C2-C1-C6 120.4723 C11-C10-C15 126.2943
C2-C1-H7 119.7632 C3-C11-C10 102.7679
C6-C1-H7 119.7642 C3-C11-H12 109.673
C1-C2-C3 118.0400 C3-C11-H13 113.0355
C1-C2-H8 120.9765 C10-C11-H12 109.5953
C3-C2-H8 120.9816 C10-C11-H13 113.1131
C2-C3-C4 121.0377 H12-C11-H13 108.5238
C2-C3-C11 127.4879 C10-C15-H16 120.0000
C4-C3-C11 111.4744 C10-C15-C17 120.0000
C3-C4-C5 121.9774 H16-C15-C17 120.0000
C3-C4-C9 109.4829 C15-C17-C18 124.7642
C5-C4-C9 128.5221 C15-C17-S24 124.7746
C4-C5-C6 117.7663 C18-C17-S24 110.4606
C4-C5-H25 121.1189 C17-C18-C20 113.5126
C6-C5-H25 121.1129 C17-C18-H21 123.2476
C1-C6-C5 120.3292 C20-C18-H21 123.2358
C1-C6-H26 119.8356 C20-C19-H22 124.7639
C5-C6-H26 119.8346 C20-C19-S24 110.4606
C4-C9-C10 105.8247 H22-C19-S24 124.7749
C4-C9-O14 127.0637 C18-C20-C19 113.5128
C10-C9-O14 127.0972 C18-C20-H23 123.2357
C9-C10-C11 107.4392 C19-C20-H23 123.2475
C9-C10-C15 126.2653 C17-S24-C19 90.8338

Table 3. Optimized geometrical parameters of PMDHI by DFT/B3LYP with 6-311G (d,p) basis set.

Bond Bond length (Å) Bond Bond length (Å)

C1-C2 1.5272 C7-H21 1.0700
C1-C9 1.5327 C8-C9 1.5301
C1-O10 1.2584 C8-H22 1.0700
C2-C3 1.5392 C11-C13 1.5400
C2-C11 1.3552 C11-H23 1.0700
C3-C4 1.5534 N12-C13 1.4838
C3-H17 1.0700 N12-C16 1.4838
C3-H18 1.0700 N12-H24 1.0000
C4-C5 1.5315 C13-C14 1.3500
C4-C9 1.3464 C14-C15 1.5223
Chem. Proc. 2022, 4, x FOR PEER REVIEW 5 of 9

C5-C6 1.3646 C14-H25 1.0700

C5-H19 1.0700 C15-C16 1.3500
C6-C7 1.5575 C15-H26 1.0700
C6-H20 1.0700 C16-H27 1.0700
C7-C8 1.3633 - -

Table 4. Optimized geometrical parameters of PMDHI by DFT/B3LYP with 6-311G (d,p) basis set.

Bond Bond Angle (°) Bond Bond Angle (°)

C2-C1-C9 105.6284 C7-C8-C9 117.9669
C2-C1-O10 127.1953 C7-C8-H22 121.0126
C9-C1-O10 127.1619 C9-C8-H22 121.0186
C1-C2-C3 106.8042 C1-C9-C4 110.0000
C1-C2-C11 126.5817 C1-C9-C8 128.2495
C3-C2-C11 126.6127 C4-C9-C8 121.7324
C2-C3-C4 102.6254 C2-C11-C13 120.0000
C2-C3-H17 109.6314 C2-C11-H23 120.0000
C2-C3-H18 113.1576 C13-C11-H23 120.0000
C4-C3-H17 109.6918 C13-N12-C16 102.7785
C4-C3-H18 113.0973 C13-N12-H24 110.3561
H17-C3-H18 108.5029 C16-N12-H24 110.3556
C3-C4-C5 127.2496 C11-C13-N12 124.9617
C3-C4-C9 111.9489 C11-C13-C14 124.948
C5-C4-C9 120.8014 N12-C13-C14 110.0899
C4-C5-C6 118.2202 C13-C14-C15 107.1612
C4-C5-H19 120.8915 C13-C14-H25 126.4278
C6-C5-H19 120.8864 C15-C14-H25 126.4037
C5-C6-C7 120.5217 C14-C15-C16 107.1615
C5-C6-H20 119.7384 C14-C15-H26 126.4035
C7-C6-H20 119.7395 C16-C15-H26 126.4276
C6-C7-C8 120.3807 N12-C16-C15 110.0898
C6-C7-H21 119.8099 N12-C16-H27 124.9621
C8-C7-H21 119.8088 C15-C16-H27 124.9476

3.2.2. HOMO-LUMO and Reactivity Descriptor’s Study

The highest occupied molecular orbital (HOMO) and lowest unoccupied orbital
(LUMO) are collectively called frontier molecular orbitals (FMO). The FMO provides a lot
of information about the stability and reactivity of molecules. Understanding several fun-
damental electronic aspects of the molecules requires an understanding of the energy gap
between FMOs. TD-DFT/B3LYP method at 6-311G(d,p) basis set is used to obtain the
HOMO-LUMO orbitals of the compounds under study. The HOMO-LUMO of TMDHI
and PMDHI compounds are shown in Figure 2. The electronic parameters are given in
Table 5. It is evident from the HOMO-LUMO energy data that the PMDHI compound has
a more reactive HOMO and the TMDHI compound has a more reactive LUMO. Both ion-
ization potential and electron affinity value of TMDHI are greater than PMDHI com-
pound. The difference in energy gap value (ΔE) in TMDHI and PMDHI is negligible (Ta-
ble 5). Also, the TMDHI compound has a slightly more inevitable charge transfer phe-
nomenon which is validated by the charge transfer value (ΔNmax in Table 6). Using
Koopman’s theorem [22], various global reactivity parameters such as chemical hardness
(ɳ), chemical softness (σ), global electrophilicity (ω), electronegativity (χ), and chemical
potential (μ) have been calculated from HOMO-LUMO energy values. The chemical hard-
ness and softness values suggest that both compounds are polarizable. The TMDHI com-
pound has more electrophilicity index as compared to PMDHI.
Chem. Proc. 2022, 4, x FOR PEER REVIEW 6 of 9

Figure 2. HOMO-LUMO representation of TMDHI and PMDHI at TD-DFT B3LYP/6-311G(d,p) ba-

sis set.

Table 5. Electronic parameters.

Electronic
TMDHI PMDHI
Parameters
ETotal (a.u.) −1013.08 −670.25
EHOMO (eV) −6.23 −5.81
ELUMO (eV) −2.40 −2.12
I (eV) 6.23 5.81
A (eV) 2.40 2.12
ΔE (eV) 3.83 3.69

Table 6. Global reactivity parameters.

Global Reactivity Parameters TMDHI PMDHI

ɳ (eV) 1.91 1.84
σ (eV−1) 0.52 0.54
ω (eV) 4.95 4.26
Χ (eV) 4.35 3.96
μ (eV) − 4.35 − 3.96
ΔNmax (eV) 2.28 2.15

3.2.3. Mulliken Atomic Charges and MESP Analysis TMDHI and PMDHI
The Mulliken population analysis [23] gives rise to Mulliken’s charges. It explains
how to use computational simulations to calculate partial atomic charges. Mulliken’s
charges are those that are based on charge density. Tables 7 and 8 show the Mulliken
atomic charges of TMDHI and PMDHI, respectively. The graphical presentation of Mul-
liken´s atomic charges in Figure 3 revealed that all hydrogen atoms in both compounds
have a positive charge. The most negative and positive carbon atoms in TMDHI, accord-
ing to Mulliken’s population analysis, are C17 (-0.289104) and C9 (0.229276), respectively.
On the other hand, C2 (−0.212715) and C1 (0.233053) are the most negative and positive
carbon atoms in PMDHI. Also, Figure 4 characterizes the Molecular Electrostatic Surface
Chem. Proc. 2022, 4, x FOR PEER REVIEW 7 of 9

Potential plot (MESP) and Contour plot of TMDHI and PMDHI. MESP correlates a mole-
cule’s total charge distribution with its dipole moment, electronegativity, partial charges,
and chemical reactivity site which provides a visual technique for understanding a mole-
cule’s relative polarity and can be used to illustrate hydrogen bonding, reactivity, and the
structure-activity relationship. It’s a proton’s potential energy at a specific position near a
molecule. Different colors correspond to different values of the electrostatic potential at a
molecule’s surface. In general, locations with attracting potential are red, whereas those
with repulsive potential appear blue. In the title compounds, the negative potential is lo-
cated around oxygen atoms.

Figure 3. Graphical representations of Mulliken atomic charges of TMDHI and PMDHI.

Table 7. Mulliken atomic charges of TMDHI.

Atom Charge Atom Charge

1 C −0.076750 14 O −0.311977
2 C −0.072450 15 C 0.064495
3 C −0.126599 16 H 0.112672
4 C −0.050045 17 C −0.289104
5 C −0.025596 18 C −0.017300
6 C −0.090894 19 C −0.279449
7 H 0.100220 20 C −0.078322
8 H 0.084509 21 H 0.104101
9 C 0.229276 22 H 0.136900
10 C −0.217264 23 H 0.104287
11 C −0.091529 24 S 0.297920
12 H 0.145453 25 H 0.101314
13 H 0.145448 26 H 0.100684

Table 8. Mulliken atomic charges of PMDHI.

Atom Charge Atom Charge

1 C 0.233053 15 C −0.174635
2 C −0.212715 16 C 0.071373
3 C −0.117113 17 H 0.137003
4 C −0.125741 18 H 0.137010
5 C −0.074563 19 H 0.081793
6 C −0.078164 20 H 0.098929
7 C −0.090555 21 H 0.099950
8 C −0.027462 22 H 0.100748
9 C −0.050736 23 H 0.109267
Chem. Proc. 2022, 4, x FOR PEER REVIEW 8 of 9

10 O −0.318016 24 H 0.230848
11 C 0.027235 25 H 0.096810
12 N −0.397939 26 H 0.096999
13 C 0.169697 27 H 0.107705
14 C −0.130779 - -

Figure 4. Molecular electrostatic surface potential plot (MESP) and Contour plot of TMDHI and
PMDHI.

4. Conclusions
In conclusion, we have studied two chalcone derivatives of 2,3-dihydro-1H-inden-1-
one: (E)-2-(thiophen-2-ylmethylene)-2,3-dihydro-1H-inden-1-one (TMDHI) and (E)-2-
((1H-pyrrol-2-yl)methylene)-2,3-dihydro-1H-inden-1-one (PMDHI). Using DFT at
B3LYP/6-311G(d,p) basis package, a detailed structural study has been performed by ex-
act molecular structure, bond length, and bond angle. Both compounds have C1 point
group symmetry, meaning that the compounds are overall asymmetric. The unavoidable
charge transfer phenomenon occurs in both compounds. The carbonyl bond length in
TMDHI (C9-O14) and PMDHI (C1-O10) is nearly 1.26 Å . The olefinic in both TMDHI (C10-
C15) and PMDHI (C2-C11) is exactly the same which is 1.3552 Å . Other bond lengths are
also in agreement with the optimized structures. Bond angle data of both compounds are
also in good agreement. PMDHI (4.97 Debye) appears to be more polar than TMDHI (4.28
Debye) based on the dipole moment data. The augmentation in the dipole moment in
PMDHI is obviously due to the presence of a more electronegative nitrogen atom. The
total energy of TMDHI is less than PMDHI compound suggesting that TMDHI compound
is less reactive and more stable. The Mulliken’s atomic charges analysis revealed that all
hydrogen atoms in both compounds have a positive charge. The Mulliken’s atomic
charges analysis revealed that all hydrogen atoms in both compounds have a positive
charge. The most negative and positive carbon atoms in TMDHI, according to Mulliken’s
population analysis, are C17 (−0.289104) and C9 (0.229276), respectively. On the other
hand, C2 (−0.212715) and C1 (0.233053) are the most negative and positive carbon atoms
in PMDHI.

Acknowledgments: The Authors acknowledge the central instrumentation facility (CIF), Savitribai
Phule Pune University, Pune for the spectral analysis and CIC, KTHM College, Nashik for FT-IR
spectral analysis. The authors are also grateful to A. B. Sawant for the Gaussian study. Aapoorva P.
Hiray, Coordinator of M. G. Vidyamandir institute is gratefully acknowledged for the Gaussian
package.
Chem. Proc. 2022, 4, x FOR PEER REVIEW 9 of 9

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