How To Read and Interpret 1H-NMR and 13C-NMR

267
Indonesian Journal of Science & Technology 6 (2) (2021) 267-298
Indonesian Journal of Science & Technology

Journal homepage: http://ejournal.upi.edu/index.php/ijost/
How to Read and Interpret 1H-NMR and 13C-NMR

Spectrums
Ramdhan Gunawan, Asep Bayu Dani Nandiyanto*
Departemen Kimia, Universitas Pendidikan Indonesia, Jl. Setiabudi No. 229, Bandung, Indonesia
Correspondence: E-mail: [email protected]
ABSTRACTS ARTICLE INFO

Article History:
Nuclear magnetic resonance spectroscopy or NMR is a Received 30 Oct 2020
Revised 10 Feb 2021
chemical instrument that can be used to evaluate the
Accepted 15 Mar 2021
structure of a chemical compound other than FTIR, GC-MS, Available online 20 Mar 2021
and HPLC. NMR spectroscopy commonly used for compound ____________________
analysis is 1H-NMR and 13C-NMR. Techniques can be used to Keywords:
1
determine the structure conformation, the number of H-NMR,
13
protons, and the number of carbons in the structure of a C-NMR,
spectra,
chemical compound. So far, there have been many spectroscopy
publications related to the use of this spectroscopic
technique. However, the steps in reading and interpreting
the spectra of both 1H-NMR and 13C-NMR are not described
in detail. Thus, in this paper, we described the steps in
reading and interpreting the 1H-NMR and 13C-NMR spectra
based on the level of difficulties: (1) simple compounds, (2)
fairly complex compounds, (3) more complex compounds,
and (4) very complex compounds.
© 2021 Tim Pengembang Jurnal UPI

Gunawan and Nandiyanto How to Read and Interpret 1H-NMR and 13C-NMR … | 268
1. INTRODUCTION levodopa compounds using 1H-NMR

conducted by Talebpour et al. (2004),
A nuclear magnetic resonance analysis of eugenol compounds. which
spectrometer (NMR) is a chemical were extracted from cloves using 1H-NMR
instrument used to obtain information and 13C-NMR (Thirukumaran et al., 2014),
regarding the structure and conformation pyrazole-based ligand analysis
of a chemical compound. NMR (Bouroumane et al., 2021), and others. In
spectroscopy is a fairly good method of addition to qualitative use, NMR
elucidation in determining the structure of spectroscopy can also be used for
organic compounds. NMR spectroscopy quantitative analysis purposes (Fernandez-
utilizes the interaction between the nucleus Pastor et al. (2019)). However, the reading
which acts as a small magnet and an and interpretation of the 1H-NMR and 13C-
external magnetic field, making it NMR spectra were not described in detail.
applicable for evaluating chemical bonds
Based on our previous studies on the
and the nuclear environment (Dayrit & de
data interpretation of FTIR and adsorption
Dios, 2017). The signal obtained from NMR
isotherm (Nandiyanto et al., 2019;
spectroscopy provides information about
Ragadhita & Nandiyanto, 2021), the
the interactions between nuclei and
purpose of this study was to explain how to
electrons as well as interactions between
read and interpret the 1H-NMR and 13C-
nuclei, which can help to determine the
NMR spectra through step-by-step
structure of a chemical compound (Hilal et
exposure in determining simple
al., 2017). The resulting NMR spectrum is a
compounds, fairly complex compounds,
collection of one or more resonant peaks at
more complex compounds, and very
a certain frequency.
complex compounds. Interpreting is very
There are two types of NMR important since it can allow researchers
spectroscopy, namely 1H-NMR and 13C- and practitioners for further analyses
NMR. One of the important pieces of (Mohamad et al., 2021).
information that the 1H-NMR spectrum
shows is the chemical shifts of the different 2. CURRENT THEORIES FOR 1H-NMR AND
13C-NMR SPECTRUM
types of protons in the sample, whereas
13C-NMR can provide structural information Spectrum in the 1H-NMR and 13C-
related to a compound based on the NMR Analysis Result
1H-NMR spectroscopy is an analytical
chemical shifts of various types of carbon.
Apart from being used to determine the method used to determine the structure of
structure of chemical compounds, NMR a compound based on the type of proton or
spectroscopy can also be used in advanced hydrogen. The 1H-NMR spectrum provides
medical imaging techniques, such as MRI. information regarding the number of
NMR has now become an analytical proton types in a compound and the
technology that can be applied in many
environmental properties of each type of
disciplines of research, medicine, and
hydrogen proton. According to Harwood
various industries (Hameed et al., 2017).
and Claridge (1997), there is some
Many studies have described the important information appearing in the 1H-
application of 1H-NMR and 13C-NMR NMR spectrum, such as
spectroscopy in the analysis of the structure
of a chemical compound, especially organic 1) The proton resonance is distributed
compounds such as the analysis of along the frequency axis. Each proton is
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269 | Indonesian Journal of Science & Technology, Volume 6 Issue 2, Sept 2021 Hal 267-298
in a different chemical environment thus giving the effect of magnetic field

characterized by its chemical shift (δ). induction. In addition to the induction
effect of the presence of electronegative
2) Different peaks in the spectrum can be
atoms such as N and O, chemical shifts are
seen appearing with different
also influenced by the anisotropy of a
intensities which related to the number
chemical bond, such as compounds with
of protons giving rise to the signal.
alkene (C=C), alkynes (C≡C), carbonyl (C=O),
3) Multiple proton resonances can and aromatic (Ar) groups. The peaks appear
interact with neighboring atoms. The at a greater chemical shift in the presence
degree of interaction or coupling is of the double bond.
indicated by the coupling constant (J).
In contrast to 1H-NMR, the absorption
The absorption peak that appears in the peak shown in the 13C-NMR spectrum
1H-NMR spectrum is represented by the provides structural information based on
difference in the resonance frequency of a the chemical shifts of various types of
nucleus against the standard in units of ppm carbon in a chemical compound. The
or chemical shift (δ). The value of chemical schematic of the 13C-NMR spectral peaks
shift (δ) is influenced by several factors, for various types of proton absorption is
such as: (1) inductive effect, (2) bond shown in Figure 2. The chemical shift of
anisotropy, and (3) hydrogen bond carbon is determined by the type of carbon
formation. The schematic of the 1H-NMR bond itself. The carbonyl carbon (C=O) is
spectral peaks for various types of proton highly de-shielded and has a larger chemical
absorption is shown in Figure 1. shift value, the carboxylate and ester
groups have smaller chemical shift values.
Figure 1 shows that the inductive effect Ketone and aldehyde groups have a
of an electronegative atom such as oxygen chemical shift value of around 200 ppm,
and nitrogen causes peaks to appear in while aromatic carbon has a chemical shift
large chemical shifts, known as de-shielded. value of between 110–160 ppm. Carbon
This can occur because an electronegative with double bonds has a chemical shift
atom such as O has the direction of the value between 100–50 ppm, metine,
electron cloud circulation in the same methylene, and methyl have a chemical
direction as the external magnetic field, shift value between 10–50 ppm.
Figure 1. Chemical shift (δ) of the 1H-NMR spectra
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Figure 2. Chemical shift (δ) 13C-NMR spectra

neighboring protons. This identification
is done to determine the multiplicity or
Step-by-step Analysis Procedure
peak pattern that appear in the 1H-
1
2.2.1 H-NMR Spectra NMR spectrum.
There are six primary steps in reading
and interpreting the 1H-NMR spectrum, There are several patterns of signal
including: multiplicity in the 1H-NMR spectrum as
follows:
1) Step 1: Identify the number of signals
that appear by observing the chemical a) Singlet: Protons without
environment of the structure of the neighboring protons that are not
compound being analyzed. The signal magnetically equivalent show a
that appears represents the difference single peak in the 1H-NMR
in the chemical environment of the spectrum.
hydrogen atom in a molecule. For b) Doublet: Protons with one non-
example, Figure 3 shows the structure equivalent neighboring proton give
of the compound p-cymene. rise to a peak that is split in half or
double.
c) Triplet: A proton with two
neighboring protons that are not
equivalent to each other give rise to
a peak that is split into three.
d) Quartet: A proton with three
neighboring protons that are not
Figure 3. Structure of p-cymene
equivalent to each other give rise to
The p-cymene structure shows the a peak that is split into four.
presence of CH and CH3 groups that are 3) Step 3: Identify the signal integration
in the same chemical environment as value. Integration shows the relative
shown in Figure 3. CH and CH3 groups number of H obtained from the
that are in the same chemical measurement of the length of each
environment are shown as one peak. The greater the integration value,
spectrum peak so that the p-cymene the more protons that generate the
compound give rise to five spectral signal.
peaks. 1H-NMR. 4) Step 4: Identify the peaks based on the
chemical shift value (δ). Chemical shift
2) Step 2: Identify the multiplicity of values for certain types of protons in a
signals that arise due to the presence of
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particular group. The chemical shift TMS is called de-shielded. The value of
value (δ) of a nucleus arises as a result chemical shift (δ) is influenced by
of the presence of electrons in a several factors, such as: (1) inductive
molecule which forms a shielding effect effect, (2) bond anisotropy, and (3)
on the spin of the nucleus. An atom hydrogen bond formation. The
with a low or near TMS chemical shift chemical shift values in 1H-NMR
value is called shielded, while a high or spectroscopy are shown in Table 1.
distant chemical shift (δ) value with
Table 1. Chemical shift 1H-NMR
Type of Bond Chemical shift (δ) (ppm) Description

R-CH3 0.9 Alkyl (methyl)
R-CH2-R 1.3 Alkyl (methylene)
R3C-H 1.5 – 2 Alkyl (methine)
1.8 Alylic
2 – 2.3 CH α – carbonyl (C=O)
2.3 Benzylic (C-Ph)

2.5 Alkynyl
2–3 CHα – N
2–4 CHα – halogen (Cl, Br, I)
3.8 CHα – oxygen
4.5 CHα – fluorine
7.3 Aromatic
9.7 Aldehyde
ROH 0.5 – 5 Alcohol

ArOH 4–7 Phenol
10 – 13 Carboxylic acid
RNH2 0.5 – 5 Amine

ArNH2 3–5 Aniline
5–9 Amide
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5) Step 5: Identify the coupling constant naptalene with an ortho position has a
(J). The coupling constant 13C-1H has a J value of about 8.3, meta 1.3, and para
value ranging from 125 to 250 Hz 0.7 Hz.
depending on the character of the C to 6) Step 6: From steps 1 - 5, the structure
H bond and the C and C bond. This step of an organic compound can be
can be done if the coupling constant determined. The analysis results were
data is shown on the spectrum. The combined and concluded the structural
value of the coupling constant is shown results from the NMR spectrum. First,
in Figure 3. The value of the coupling after the number of proton types and
constant (J) in Figure 3 reflects the the chemical environment of the
existence of the bonding environment protons are known in step 1, the
of a nucleus. The J value of a proton is molecular formula based on their bond
so specific that a lot of information can with H can be determined. Second, the
be retrieved. For example, a double signal multiplicity analysis provides
bond can take two forms, namely cis information on how many hydrogen
and trans. For trans double bonds have atoms are present in the adjacent
a J value between 12-18 Hz, cis carbon atoms. Finally, the pieces of the
between 6-11 Hz, and geminal molecule are combined to form a
between 0–3 Hz. The J value of an structural formula for the compound.
aromatic also provides important The coupling constant obtained in the
information about the position of the previous step shows the interactions
functional group in an aromatic. The between the protons and the chemical
proton signal of a benzene derivative shift values obtained are then
with an ortho position has a J value of compared with the chemical shift table
7.5 Hz, a meta of about 1.5 Hz and a values (Table 1) to identify their
para has a J value of 0.7 Hz, whereas a functional groups.
Figure 3. Coupling constant value (J)
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2.2.2 13
C-NMR Spectra same chemical environment giving rise
The steps for interpreting the 13C-NMR to three peaks of the 13C-NMR
spectrum of a compound are almost the spectrum.
same as determining the 1H-NMR spectrum
and are described as follows:
that appear on the 13C-NMR spectrum.
The number of carbon atoms (C) can be
determined by looking at the number Figure 4. Structure of pentane-2,4-
of peaks that appear and the chemical dione
environment of the carbon in the
compound. Just like 1H-NMR, carbon 2) Step 2: Identify the chemical shift value
atoms that are in a chemical (δ) that appears in the 13C-NMR
environment appear as the same peak. spectrum. To predict the chemical
For example, the pentane-2,4-dione shear value that appear in the 13C-NMR
compound shown in Figure 4 has five spectrum, you can use the references
carbon atoms with two of them in the in Table 2.
Table 2 Chemical shift 13C-NMR
Approximate Approximate
Type of Carbon Type of Carbon
Chemical Shift (ppm) Chemical Shift (ppm)
(CH3)4Si 0 C-I 0 – 40
R-CH3 8 – 35 C-Br 25 – 65
R-CH2-R 15 – 50 C-Cl 35 – 80
20 – 60 C-N 40 – 60
30 – 40 C-O 50 – 80
65 – 85 165 – 175
100 – 150 165 – 175
110 – 170 205 – 220
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3) Step 3: The structure of an organic 4. RESULTS AND DISCUSSION

compound can be determined by Determination of the structure of an
combining the results of the analysis organic compound can be done by
based on steps 1 and 2. First, after the analyzing the resulting 1H-NMR and 13C-
amount of carbon and its chemical NMR spectral patterns. NMR spectrum
environment are known, the molecular analysis can be performed based on the
formula of a compound can be step-by-step analysis described in section
determined. Then, the chemical shift 2.2. Analysis was carried out on the 1H-NMR
values are compared with the chemical spectrum to determine the number and
shift table values (Table 2) and the type of H atoms present in the structure of
pieces of the molecules are combined the compound. Then, the analysis of the
to form a structural formula for the 13C-NMR spectrum was carried out to
compound. obtain information regarding the number

and type of carbon atom bonds. Thus, the
3. EXPERIMENTAL METHOD structure of an organic compound can be
To understand how to read and interpret determined by combining the results of 1H-
the 1H-NMR and 13C-NMR spectra, this NMR and 13C-NMR spectrum analysis.
paper explained step by step reading the
1H-NMR and 13C-NMR spectra through step-
by-step exposure in determining simple

compounds, fairly complex compounds,
more complex compounds, and very
complex compounds. The simple
compound used are: methane, methanol,
acetylene, n-octane, and iso-butane. The
fairly complex compound used are: toluene
and naphtalene. The more complex
compound used are: eugenol
(Thirukumaran et al., 2014). The very
complex compound used are: L1 – L4 ligands Figure 5. Structure of prepared mono-
(Bouroumane et al., 2021). alkylated pyrazole L1-L4 (Bouroumane et
Thirukumaran et al. (2014) conducted al., 2021)
NMR spectroscopic analysis of eugenol
compounds extracted from clove plants.
NMR spectroscopy was performed using a 4.1. NMR Analysis of Simple Compound
Joel spectrometer with tetramethylsilane 4.1.1. NMR Spectra of Methane
1H-NMR and 13C-NMR spectra of
(TMS) as the internal standard and samples
were prepared using CDCl3 and methane are shown in Figures 6 and 7,
(Bouroumane et al., 2021) synthesize N- respectively. Based on a step-by-step
alkylated pyrazolyl compound (L1-L4) via analysis of how to read and interpret the
1H-NMR and 13C-NMR spectrum, the
one-step process by condensation of (3,5-
dimethyl-1Hpyrazol-1-yl) methanol A with a interpretation is described in the following.
appropriate primary amines using DMSO
solvent system and the structure of L1-L4
compound are shown in Figure 5.
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Figure 6. Methane 1H-NMR Spectra

(https://scilearn.sydney.edu.au/OrganicSpectroscopy/?type=NMR&page=Examples,
retrieved on 29 October 2020)
Figure 7 Methane 13C-NMR spectra

4.1.1.1. 1H-NMR Spectra Analysis 2) Step 2: Identify the multiplicity of

1) Step 1: Identify the number of signals signals that arise due to the presence of
that appear. Figure 6 presents one neighboring protons. Figure 6 shows
peak (A), indicating a signal originating signal (A) appears as a singlet peak,
from one type of proton. indicating the absence of a proton in
the neighboring C atom.
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3) Step 3: Identify the signal integration analyzes in Figures 6 and 7 are combined, a
value. Figure 6 shows the peak (A) CH4 (methane) compound is formed.
appears with the integration value for
4.1.2. NMR Spectra of Methanol
four H atoms, showing that the four H 1H-NMR and 13C-NMR spectra of
atoms are in the same chemical
methanol are shown in Figures 8 and 9,
environment. Thus, they appear as one
respectively.
peak.
4) Step 4: Identify the peaks based on the 4.1.2.1. 1H-NMR Spectra Analysis
chemical shift value (δ). Based on the 1) Step 1: Identify the number of signals
reference data in Table 1, Figure 6 that appear. Figure 8 displays two
displays the peaks appear at 0.23 ppm peaks that appears (A) and (B) which
close to the chemical shift value of the indicates a signal originating from two
methyl R-CH3 (0.9 ppm). However, in types of proton.
step 3 it is explained that the peaks 2) Step 2: Identify the multiplicity of
have integration for four H atoms, so signals that arise due to the presence of
that there is no inductive effect or bond neighboring protons. Figure 8 shows
anisotropy effect, causing the peaks to signal (A) and (B) appears as a singlet
appear at a smaller chemical shift (0.23 peak, respectively indicating the
ppm). absence of a proton in the neighboring
C atom.
4.1.1.2. 13C-NMR Spectra Analysis 3) Step 3: Identify the signal integration
1) Step 1: Identify the number of signals. value. Figure 8 shows the peak (A)
Figure 7 shows one peak that appears appears with the integration value for
(A) which indicates a signal originating three H atoms, meanwhile peak (B)
from one type of carbon. appears with the integration for one H
2) Step 2: Identify the chemical shift value atom.
(δ). Based on the reference data in 4) Step 4: Identify the peaks based on the
Table 2 and Figure 2, Figure 7 shows chemical shift value (δ). Based on the
the peaks appear at -2.3 ppm related to reference data in Table 1, the value of
13C sp3.
the proton chemical shift can be
determined. Figure 8 shows the peak
The 1H-NMR analysis shows the signal (A) appear at 3,48 ppm to 3 ×
appears as a singlet peak with integration 1H on sp3 CH group bonded to the
3
values for four H atoms and appears at 0.23 electronegative OH group and peak (B)
ppm, whereas the 13C-NMR analysis appear at 4.3 ppm related to 1H on
showed that there was one peak indicating OH group as a broad peak caused by
the presence of one carbon atom and the 1H rapidly exchanges with 1H atoms
appeared at -2.3 ppm referring to the C sp3 in the solvent.
atom. Thus, if the 1H-NMR and 13C-NMR
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Figure 8 Methanol 1H-NMR Spectra

Figure 9 Methanol 13C-NMR Spectra

to 13C on sp3 CH3 group bonded to the
4.1.2.2. 13C-NMR Spectra Analysis electronegative OH group.
1) Step 1: Identify the number of signals. Based on the 1H-NMR and 13C-NMR
Figure 9 shows one peak that appears spectrum analysis in Figures 8 and 9,
(A) which indicates a signal originating respectively, the 1H-NMR analysis shows
from one type of carbon. the signal appears as two peaks (A) and (B)
2) Step 2: Identify the chemical shift value at 3.48 and 4.4 ppm. Meanwhile, the 13C-
(δ). Based on the reference data in NMR analysis showed that there was one
Table 2 and Figure 2, Figure 8 shows peak at 45.9 ppm indicating
the peaks appear at 45.9 ppm related 13C on sp3 CH group bonded to the
3
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electronegative OH group. Thus, if the 1H- 9 are combined, a CH3OH (methanol)

NMR and 13C-NMR analyzes in Figures 8 and compound is formed.
4.1.3. NMR Spectra of Acetylene the proton chemical shift can be
1H-NMR and 13C-NMR
spectra of acetylene determined. Figure 8 shows the peak
are shown in Figures 10 and 11, appears at 1.91 ppm. The C-H bond
respectively. generally occurs at 0.2 – 0.9 ppm. The
peak that appears for the CH bond at
4.1.3.1. 1H-NMR Spectra Analysis greater chemical shift (1.91 ppm)
1) Step 1: Identify the number of signals appears due to the anisotropy effect of
that appear. Figure 10 shows one peak the triple bond between two carbon
that appears (A) which indicates a atoms -C≡C-.
signal originating from one type of
proton. 4.1.3.2. 13C-NMR Spectra Analysis
2) Step 2: Identify the multiplicity of 1) Step 1: Identify the number of signals.
signals. Figure 10 presents signal (A) Figure 11 shows one peak that appears
appears as a singlet peak indicating the (A), which indicates a signal originating
absence of a proton in the neighboring from one type of carbon.
C atom. 2) Step 2: Identify the chemical shift value
3) Step 3: Identify the signal integration (δ). Based on the reference data in
value. Figure 10 shows the peak (A) Table 2 and Figure 2, the value of the
appears with the integration value for carbon chemical shift can be
one H atom. determined. Figure 11 shows the peaks
4) Step 4: Identify the peaks based on the appear at 71.9 ppm related to 13C sp
chemical shift value (δ). Based on the (C≡C).
reference data in Table 1, the value of
Figure 10 Acetylene 1H-NMR Spectra
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Figure 11 Acetylene 13C-NMR Spectra
Based on the 1H-NMR and 13C-NMR 2) Step 2: Identify the multiplicity of

spectrum analysis in Figures 10 and 11, signals that arise due to the presence
respectively, the 1H-NMR analysis shows of neighboring protons. Figure 13
the signal appears as a singlet peak with an shows signal (A) appears as a multiplet
integration value for one H atoms and peak indicates the presence of several
appears at 1.91 ppm. Meanwhile, the 13C- protons on the neighboring carbon and
NMR analysis showed that there was a peak signal (B) appears as a triplet peak
indicating the presence of one type of indicates the presence of two protons
carbon atom and appeared at 71.9 ppm on the neighboring carbon.
referring to the C sp atom (C≡C). Thus, if the 3) Step 3: Identify the signal integration
1H-NMR and 13C-NMR analyzes in Figures 8 value. Figure 13 shows the peak (A)
and 9 are combined, a C2H2 (acetylene) appears with the integration value for
compound is formed and its structure twelve H atom and peak (B) appears
shown in Figure 12. with the integration value for six H
atom.
4) Step 4: Identify the peaks based on the
chemical shift value (δ). Based on the
Figure 12 Structure of Acetylene (Voronin reference data in Table 1, the value of
et al., 2018) the proton chemical shift can be
4.1.4. NMR Spectra of n-Octane determined. Figure 13 shows the peak
1H-NMR and 13C-NMR spectra of n-octane (A) appears at 1.26 ppm related to the
are shown in Figures 13 and 14, chemical shift value of the methylene
respectively. (R-CH2-R) and peak (B) appears at 0.88
ppm related to the chemical shift value
4.1.4.1. 1H-NMR Spectra Analysis of the methyl (R-CH3).
1) Step 1: Identify the number of signals 4.1.4.2. 13C-NMR Spectra Analysis
that appear. Figure 13 shows two 1) Step 1: Identify the number of signals.
peaks that appears (A) and (B) which Figure 14 shows four peaks that
indicates a signal originating from two appears (A, B, C, D), indicating a signal
types of proton. originating from four types of carbon.
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2) Step 2: Identify the chemical shift value sp3 methyl (-CH3), peak (B, C, and D)
(δ). Based on the reference data in appeared at 22.7; 29.3; and 31.9 ppm,
Table 2 and Figure 2, Figure 14 shows respectively, relating to 13C sp3
the peak (A) at 14.1 ppm related to 13C methylene (-CH2-).
Figure 13 n-octane 1H-NMR Spectra (https://www.chemicalbook.com/SpectrumEN_111-

65-9_13cnmr.htm, retrieved on 29 October 2020)
Figure 14 n-octane 13C-NMR Spectra (https://www.chemicalbook.com/SpectrumEN_111-

65-9_13cnmr.htm, retrieved on 29 October 2020)
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Based on the 1H-NMR and 13C-NMR 1) Step 1: Identify the number of signals
spectrum analysis in Figures 13 and 14, that appear. Figure 16 shows two
respectively, the 1H-NMR analysis shows peaks that appears (A) and (B) which
the signal (A) appears as a multiplet peak indicates a signal originating from two
with an integration value for twelve H types of proton.
atoms and appears at 1.26 ppm (R-CH2-R). 2) Step 2: Identify the multiplicity of
Peak (A) indicates the presence of 6 signals that arise due to the presence
methylene –(CH2)6–. Whereas signal (B) of neighboring protons. Figure 16
appears as a triplet peak indicating the shows signal (A) appears as a doublet
presence of two protons on the peak indicates the presence of one
neighboring carbon with integration values proton on the neighboring carbon and
for six H atoms and appears at 0.88 ppm (R- signal (B) appears as a multiplet peak
CH3). Peak (B) indicates the presence of indicates the presence of several
methyl bound to methylene (CH3-CH2-R). protons on the neighboring carbon.
Meanwhile, the 13C-NMR spectrum shows 3) Step 3: Identify the signal integration
the appearance of four peaks (A, B, C, and value. Figure 16 shows the peak (A)
D), each of which indicates the presence of appears with the integration value for
13C sp3 bonds for methyl (-CH ) and nine H atom and peak (B) appears with
3
methylene (-CH2-). Thus, if the 1H-NMR and the integration value for one H atom.
13C-NMR analyzes are combined, an n- 4) Step 4: Identify the peaks based on the
octane compound (C8H18) is formed and its chemical shift value (δ). Based on the
structure is illustrated in Figure 15. reference data in Table 1, Figure 16
shows the peak (A) at 0.89 ppm related
to the chemical shift value of the
methyl (R-CH3) and peak (B) appears at
Figure 15 n-octane structure
1.74 ppm related to the chemical shift
(https://pubchem.ncbi.nlm.nih.gov/compo
value for methyne (R3C-H).
und/octane#section=Information-Sources,
4.1.5.2. 13C-NMR Spectra Analysis
1) Step 1: Identify the number of signals.
Figure 17 shows four peaks appearing
4.1.5. NMR Spectra of Isobutene (A) and (B), indicating a signal
1H-NMR and 13C-NMR spectra of isobutene originating from two types of carbon.
are shown in Figures 16 and 17, 2) Step 2: Identify the chemical shift value
respectively. Based on a step-by-step (δ). Based on the reference data in
analysis of how to read and interpret the Table 2 and Figure 2, Figure 17 shows
the peak (A) appeared at 24.3 ppm,
following conclusions are: relating to 13C sp3 methyl (-CH3) and
4.1.5.1. 1H-NMR Spectra Analysis peak (B) at 25 ppm related to C sp3
methyne (-CH-).
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Figure 16 Isobutane 1H-NMR Spectra (Abraham & Mobli, 2008)
Figure 17 Isobutane 13C-NMR Spectra

Based on analysis in Figures 16 and 17, with integration values for one H atom and
respectively, the 1H-NMR analysis shows appears at 1.74 ppm (R3C-H). Peak (B)
the signal (A) appears as a doublet peak indicates the presence of methyne bound
indicating the presence of one proton on to three methyl (CH3). Meanwhile, the 13C-
the neighboring carbon with an integration NMR spectrum shows the appearance of
value for nine H atoms and appears at 0,89 two peaks (A) and (B), indicating the
ppm (R-CH3). It can be concluded that peak presence of 13C sp3 bonds for methyl (-CH3)
(A) indicates the presence of 3 methyl and methyne (-CH-). Thus, if the 1H-NMR
3(CH3), whereas signal (B) appears as a and 13C-NMR analyzes are combined, an
multiplet peak indicating the presence of isobutane compound (C4H10) is formed (see
several protons on the neighboring carbon Figure 18).
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Signal is not split by coupling as all 1H

environments are the same.
3) Step 3: Identify the signal integration
value. Figure 19 shows the peak (A)
Figure 18 Structure of isobutane appears with the integration value for
(https://www.ebi.ac.uk/chebi/searchId.do?chebiId six H atoms. All 1H environments are
=43907#:~:text=Isobutylene%20(or%202%2Dmeth
ylpropene),is%20of%20considerable%20industrial
the same causes the signal to appear as
%20value, retrieved on 29 October 2020) one peak.
4.2. NMR Analysis of Fairly Complex chemical shift value (δ). Based on the
Compound reference data in Table 1, the value of
4.2.1. NMR Spectra of Benzene the proton chemical shift can be
1H-NMR and 13C-NMR spectra of determined. Figure 19 shows the peak
benzene are shown in Figures 19 and 20, (A) appear at 7.34 ppm related to
respectively. 6×1H on sp2 CH groups.
4.2.1.1. 1H-NMR Spectra Analysis
1) Step 1: Identify the number of signals.
that appear. Figure 19 shows one peak
Figure 20 shows one peak that appears
that appears (A) which indicates a
(A) which indicates a signal originating
signal originating from one type of
from one type of carbon.
proton.
2) Step 2: Identify the chemical shift value
2) Step 2: Identify the multiplicity of
(δ). Based on the reference data in
signals that arise due to the presence
Table 2 and Figure 2, the value of the
of neighboring protons. Figure 19
carbon chemical shift can be
shows signal (A) appears as a singlet
determined. Figure 20 shows the peaks
peak indicating the absence of a
appear at 128.5 ppm related to
proton in the neighboring C atom. 13C on sp2 CH groups.
Figure 19 Benzene 1H-NMR Spectra

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Figure 20 Benzene 13C-NMR Spectra

Based on the 1H-NMR and 13C-NMR 4.2.2.1. 1H-NMR Spectra Analysis
spectrum analysis in Figures 19 and 20, 1) Step 1: Identify the number of signals
respectively, the 1H-NMR analysis shows that appear. Figure 22 shows two
the signal appears as one peak at 7.34 ppm peaks that appears (A) and (B) which
with integration for six H atoms. The signal indicates a signal originating from two
is not split by coupling due to all H 1 types of proton.
environments are the same. Meanwhile, 2) Step 2: Identify the multiplicity of
the 13C-NMR analysis showed that there signals that arise due to the presence
was one peak at 128.5 ppm indicating of neighboring protons. Figure 22
13C on sp2 CH groups. Thus, if the 1H-NMR shows both of signal (A) and (B)
and 13C-NMR analyzes in Figures 19 and 20 appears as a multiplet peak indicating
are combined, a C6H6 (benzene) compound presence of several protons in the
is formed and its structure shown in Figure neighboring C atom.
21. 3) Step 3: Identify the signal integration
value. Figure 22 shows both of peak (A)
and (B) appears with the integration
value for four H atoms.
chemical shift value (δ). Based on the
reference data in Table 1, the value of
the proton chemical shift can be
Figure 21 Structure of benzene determined. Figure 22 shows the peak
(A) appear at 7.32 ppm related to 4
× 1H on sp2 CH groups. Similar to peak
4.2.2. NMR Spectra of Naphtalene (A), peak (B) appears at 7.67 ppm
1H-NMR and 13 C-NMR spectra of related to 4 × 1H on sp2 CH groups.
naphthalene are shown in Figures 22 and
23, respectively.
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Figure 22 Naphthalene 1H-NMR Spectra

(https://www.chemicalbook.com/SpectrumEN_111-65-9_13cnmr.htm, retrieved on 29
October 2020)
Figure 23 Naphthalene 13C-NMR Spectra

(https://www.chemicalbook.com/SpectrumEN_111-65-9_13cnmr.htm, retrieved on 29
October 2020)
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4.2.2.2. 13C-NMR Spectra Analysis 1) Step 1: Identify the number of signals

1) Step 1: Identify the number of signals. that appear. Figure 25 shows eight
Figure 23 shows three peaks that peaks that appears which indicates a
appears (A), (B), and (C) indicating the signal originating from eight types of
signal from three types of carbon. proton.
2) Step 2: Identify the chemical shift value 2) Step 2: Identify the multiplicity of
(δ). Based on the reference data in signals that arise due to the presence
Table 2 and Figure 2, Figure 23 shows of neighboring protons. Figure 25
the peak (A), (B), and (C) at 125.9; presents signal (a), (b), and (c) appears
128.0; and 133 ppm respectively. All as a singlet peak indicating absence of
peaks related to 13C on sp2 CH groups. protons in the neighboring C atom.
Meanwhile signal (d), (g), and (h)
Based on the 1H-NMR and 13C-NMR appears as a doublet peak indicating
spectrum analysis in Figures 22 and 23, presence of one protons in the
respectively, the 1H-NMR analysis shows neighboring C atom and signal (e)
the signal appears as two peaks at 7.32 and appears as a multiplet peak peak
7.67 ppm with both of integration for fours indicating presence of several protons
H atoms. Meanwhile, the 13C-NMR analysis in the neighboring C atom.
showed that there was three peaks at Interestingly, signal (f) appears as a
125.9; 128.0; and 133 ppm respectively double doublet peak which indicates
indicating 13C on sp2 CH groups. Thus, if the the presence of a proton that is
1H-NMR and 13C-NMR analyzes in Figures
attached to the same C atom, but has a
22 and 23 are combined, a C10H8 very slightly different chemical shift
(naphthalene) compound is formed and its value.
structure shown in Figure 24. 3) Step 3: Identify the signal integration
value. Figure 25 shows peak (a), (c), (e),
(g), and (h) appears with the
integration value for one H atom, peak
(d) and (f) appears with the integration
value for two H atoms, and peak (b)
appears with the integration value for
Figure 24 Structure of naphthalene three H atoms.
4.3. NMR Analysis of More Complex chemical shift value (δ).
Compound Based on the reference data in Table 1,
4.3.1. NMR Spectra of Eugenol Figure 25 shows the singlet peak at 3.82
1H-NMR and 13C-NMR spectra of ppm is due to the −OCH3 protons, the
eugenol are shown in Figures 25 and 26, doublets at 3.21 and 5.05 ppm as well as
respectively. Based on a step-by-step the multiplet at 5.95 ppm are assigned to
analysis of how to read and interpret the the allyl protons [−CH2−CH=CH2−], the peak
1H-NMR and 13C-NMR spectrum, the that appear at 5.66 ppm related to −OH
following conclusions are: protons, and the peak that appears in the
range of 6.5 to 7.0 ppm is related to
4.3.1.1. 1H-NMR Spectra Analysis aromatic protons. The peak at 7.2 ppm is
due to the solvent peak (CDCl3).
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Figure 25 Eugenol 1H-NMR spectrum analysis (Thirukumaran et al., 2014)
Figure 26 Eugenol 13C-NMR spectrum analysis (Thirukumaran et al., 2014)
4.3.1.2. 13C-NMR Spectra Analysis carbon chemical shift can be

1) Step 1: Identify the number of signals. determined. Figure 26 shows the peak
Figure 26 shows nine peaks that at 56 ppm (methoxy carbons (−OCH3)),
appears which indicates a signal as well as 115; 137; and 40 ppm (alkyl
originating from nine types of carbon. carbons [−CH2−CH=CH2]), and the peak
2) Step 2: Identify the chemical shift value that appears at around 120−150 ppm is
(δ). Based on the reference data in related to aromatic carbons.
Table 2 and Figure 2, the value of the
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Based on the 1H-NMR and 13C-NMR of neighboring protons. Figure 28

spectrum analysis in Figures 25 and 26, shows the signals appear with varying
respectively, the 1H-NMR analysis shows multiplicities, indicating the presence
the signal appears as eight peaks each of multiple protons in neighboring C
representing a different type of proton atoms.
bond, such as −OCH3 protons, −OH proton, 3) Step 3: Identify the signal integration
value. Figure 28 displays several
allyl protons [−CH2−CH=CH2−], and
proton integrations, ranging from 1H,
aromatic protons. Similar to 1H-NMR
2H, and 3H.
analysis, the 13C-NMR analysis showed that 4) Step 4: Identify the peaks based on the
there was nine peaks each representing a chemical shift value (δ). Based on the
different type of carbon bond, such as reference data in Table 1, the value of
methoxy carbons (−OCH3) at 56 ppm, allyl the proton chemical shift can be
carbons [−CH2−CH=CH2] at 115 ppm, 137 determined. Figure 28 shows the peaks
ppm, and 40 ppm, and aromatic carbon at 8.02; 7.41; 6,63; and 6.56 ppm
around 120−150 ppm. Thus, if the 1H-NMR related to aromatic protons
1 2
( H on sp CH groups), peak at 7,57
and 13C-NMR analyzes in Figures 25 and 26
are combined, a C10H12O2 (eugenol) ppm is related to proton from amine
compound is formed and its structure groups (N-H), peak at 5.54 ppm is
related to 1H on sp3 CH2 groups and
presented in Figure 27.
bonded to electronegative atoms,
peak at 5.74 ppm is related to aliphatic
protons (1H on sp2 CH groups), and
peaks at 2.36 and 2.07 ppm related to
1H on sp3 CH groups.
3
Figure 27 Structure of eugenol 4.4.1.2. 13C-NMR Spectra Analysis

(Thirukumaran et al., 2014) 1) Step 1: Identify the number of signals.
From the analysis of the 13C-NMR
spectrum of the ligand L1 compound, it
4.4. NMR Analysis of Very Complex was shown that eleven peaks appeared
Compound indicating the existence of eleven
4.4.1. NMR Spectra of N-((3,5- types of carbon atoms.
dimethyl-1H-pyrazol-1- 2) Step 2: Identify the chemical shift value
(δ). Based on the reference data in
yl)methyl)pyridin-2-amine (L1 Ligand)
1H-NMR Table 2 and Figure 2, the value of the
and 13C-NMR spectra of L1
carbon chemical shift can be
ligand are shown in Figures 28 and 29,
determined. Figure 29 shows that the
respectively. peaks that appear at 157.6; 146.4; and
4.4.1.1. 1H-NMR Spectra Analysis 139.3 ppm related to 13C on sp2 bond
1) Step 1: Identify the number of signals with electronegative atom such as N,
that appear. Figure 28 shows nine peaks at 147.7; 137.5; 113.4; and 105.1
peaks that appears which indicates a related to 13C on sp2 CH, peaks at 13.8
signal originating from nine types of and 11.2 ppm related to
13C on sp3 methyl (CH ), and peak at
proton. 3
2) Step 2: Identify the multiplicity of 53.9 ppm related to 13C on sp3 CH2
signals that arise due to the presence bonded to electronegative atom.
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Figure 28 L1 ligand 1H-NMR spectra (Bouroumane et al., 2021)
Figure 29 L1 ligand 13C-NMR spectra (Bouroumane et al., 2021)
Based on the 1H-NMR and 13C-NMR electronegative atom, singlet peak at 5.74
spectrum analysis above, the 1H-NMR ppm related to aliphatic protons
analysis shows the signal appears as nine (1H on sp2 CH groups), and singlet peaks at
peaks at 8.02 and 6.63 ppm as doublet 2.36 and 2.07 ppm related to
peaks as well as 7.41 and 6.56 ppm as a 1H on sp3 CH groups. Meanwhile, the 13C-
3
triplet peak related to aromatic protons NMR analysis showed that there were
(1H on sp2 CH groups), triplet peak at 7.57 peaks at 157.6; 146.4; and 139.3 ppm
ppm related to proton from amine groups related to 13C on sp2 bond with
(N-H), doublet peak at 5.54 ppm related to electronegative atom, peaks at 147.7;
1H on sp3 CH groups bonded with 137.5; 113.4; and 105.1 ppm related to
2
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13C on sp2 CH peaks at 13.8 and 11.2 ppm 4) Step 4: Identify the peaks based on the
related to 13C on sp3 methyl (CH3), and peak chemical shift value (δ). Based on the
at 53.9 ppm related to 13C on sp3 CH2 reference data in Table 1, the value of
bonded to electronegative atom. Thus, if the proton chemical shift can be
the 1H-NMR and 13C-NMR analyzes are determined. Figure 31 shows the peaks
combined, N-((3,5-dimethyl-1H-pyrazol-1- at 8.03; 7.49; and 6.66 ppm related to
aromatic protons
yl)methyl)pyridin-2-amine compound is 1 2
( H on sp CH groups), a peak at 7,81
formed and its structure shown in Figure
ppm is related to proton from amine
30. groups (N-H), a peak at 5.42 ppm is
related to 1H on sp3 CH2 groups and
bonded to electronegative atoms,
peak at 5.74 ppm related to aliphatic
protons (1H on sp2 CH groups), and
peaks at 2.33 and 2.07 ppm related to
1H on sp3 CH groups.
3
Figure 30 Structure of L1 ligand 1) Step 1: Identify the number of signals.
(Bouroumane et al., 2021) From the analysis of the 13C-NMR
spectrum of the ligand L1 compound, it
4.4.2. NMR Spectra of 5-chloro-N-
was shown that eleven peaks appeared
((3,5-dimethyl-1H-pyrazol-1-
indicating the existence of eleven types
yl)methyl)pyridin-2-amine (L2 Ligand) of carbon atoms.
1H-NMR and 13C-NMR spectra of L2 2) Step 2: Identify the chemical shift value
ligand are shown in Figures 31 and 32, (δ). Based on the reference data in
respectively. Based on a step-by-step Table 2 and Figure 2, the value of the
analysis of how to read and interpret the carbon chemical shift can be
determined. Figure 32 show that the
following conclusions are: peaks that appear at 156.3; 145.7; and
139.4 ppm related to 13C on sp2 bond
4.4.2.1. 1H-NMR Spectra Analysis with electronegative atom such as N,
1) Step 1: Identify the number of signals peaks at 146.6; 137.4; 119.3; and 105.2
that appear. Figure 31 shows eight ppm related to 13C on sp2 CH, peaks at
peaks that appears which indicates a 13.8 and 11.1 ppm related to
signal originating from eight types of 13C on sp3 methyl (CH ), and peak at
3
proton. 53.9 ppm related to 13C on sp3 CH2
2) Step 2: Identify the multiplicity of bonded to electronegative atom. A
signals that arise due to the presence significant difference in chemical shift
of neighboring protons. Figure 31 compared to the L1 ligand was seen at
presents the signal appear with varying the peak of 119.3 ppm. In L1 ligand, the
multiplicities, indicating the presence peak appears at 113.4 ppm. In L2
of multiple protons in neighboring C ligands, the peaks appear at a larger
atoms. chemical shift. This is probably due to
3) Step 3: Identify the signal integration the presence of electronegative
value. Figure 31 shows several proton substituents such as halogens.
integrations, ranging from 1H, 2H, and
3H.
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Figure 31 L2 ligand 1H-NMR spectrum analysis (Bouroumane et al., 2021)
Figure 32 L2 ligand 13C-NMR spectrum analysis (Bouroumane et al., 2021)
Based on the 1H-NMR and 13C-NMR peak at 5.42 ppm that related to
spectrum analysis in Figures 31 and 32, 1H on sp3 CH groups bonded with
2
respectively, the 1H-NMR analysis shows electronegative atom, singlet peak at
the signal appears as nine peaks at 8.03 5.74 ppm that related to aliphatic
and 6.66 ppm as doublet peaks and 7.49 protons (1H on sp2 CH groups), and
ppm as a triplet peak that related to singlet peaks at 2.33 and 2.07 ppm that
aromatic protons (1H on sp2 CH groups), related to 1H on sp3 CH groups.
3
triplet peak at 7.81 ppm that related to Meanwhile, the 13 C-NMR analysis
proton from amine groups (N-H), doublet showed that there were peaks at 156.3;
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146.6; and 139.4 ppm that related to 3) Step 3: Identify the signal integration
13C on sp2 bond with electronegative value. Figure 34 shows several
atom, peaks at 145.7; 137.5; and 105.2 proton integrations, ranging from
ppm that related to 13C on sp2 CH, peaks 1H, 2H, and 3H.
at 13.8 and 11.1 ppm that related to 4) Step 4: Identify the peaks based on
13C on sp3 methyl (CH ), peak at 53.9 ppm the chemical shift value (δ). Based on
3
the reference data in Table 1, the
that related to C on sp3 CH2 bonded to
13
value of the proton chemical shift
electronegative atom, and peak at 119.3
can be determined. Figure 34 shows
ppm that related to 13C on sp2 bonded to the peak at 7.89 ppm appear due to
halogen atom such as Cl. Thus, if the 1H- aromatic proton
NMR and 13C-NMR analyses are 1 2
( H on sp CH groups), peak at 7.46
combined, 5-chloro-N-((3,5-dimethyl-1H- ppm appear due to proton from
pyrazol-1-yl) methyl) pyridin-2-amine amine groups (N-H), peak at 6.52 –
compound is formed and its structure 6.32 ppm appear due to
1H on sp2 CH groups, a peak at 5.73
shown in Figure 33.
ppm appear due to aliphatic protons
(1H on sp2 CH groups), peak at 5.44
appear due to 1H on sp3 CH2 groups
and bonded to electronegative
atoms, and peaks at 2.36 and 2.08
ppm appear due to aromatic and
aliphatic 1H on sp3 CH groups,
3
respectively.
Figure 33 Structure of L2 ligand 4.4.3.2. 13C-NMR Spectra Analysis

(Bouroumane et al., 2021) 1) Step 1: Identify the number of
signals. From the analysis of the 13C-
4.4.3. NMR Spectra of N-((3,5- NMR spectrum of the ligand L3
dimethyl-1H-pyrazol-1-yl)methyl)-4- compound, it was shown that twelve
methylpyridin-2-amine (L3 Ligand) peaks appeared indicating the
1H-NMR and 13C-NMR spectra of L3 existence of twelve types of carbon
ligand are shown in Figures 34 and 35, atoms.
respectively. 2) Step 2: Identify the chemical shift
value (δ). Based on the reference
data in Table 2 and Figure 2, the
value of the carbon chemical shift
that appear. Figure 34 shows seven
can be determined. Figure 35 show
peaks that appears which indicates a
that the peaks similar to L1 and L2
signal originating from seven types of
ligands. However, in Figure 35, it is
proton.
shown that there is a peak that
2) Step 2: Identify the multiplicity of
appears at 21,0 ppm indicating the
signals that arise due to the presence
presence of methyl carbon in the
of neighboring protons. Figure 34
aromatic ring while L1 and L2 do not
shows the signals appear with
show a peak for sp3 methyl carbon in
varying multiplicities, indicating the
the aromatic ring.
presence of multiple protons in
neighboring C atoms.
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Figure 35 L3 ligand 13C-NMR spectrum (Bouroumane et al., 2021)
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Based on the 1H-NMR and 13C-NMR 4.4.4. NMR Spectra of N-((3,5-

spectrum analysis in Figures 34 and 35, dimethyl-1H-pyrazol-1-yl)methyl)-6-
the 1H-NMR analysis shows the signal methylpyridin-2-amine (L4 Ligand)
appears as seven peaks : doublet peak at 1H-NMR and 13C-NMR spectra of L3
7.89 ppm related to aromatic proton ligand are shown in Figures 37 and 38,
(1H on sp2 CH groups), triplet peak at respectively.
7,46 ppm related to proton from amine
groups (N-H), multiplet peak at 6.52 –
1) Step 1: Identify the number of
6.32 ppm related to 1H on sp2 CH groups, signals that appear. Figure 37 shows
singlet peak at 5,73 ppm related to seven peaks that appears which
aliphatic protons (1H on sp2 CH groups), indicates a signal originating from
doublet peak at 5,44 related to seven types of proton.
1H on sp3 CH groups and bonded to
2 2) Step 2: Identify the multiplicity of
electronegative atoms, and singlet peaks signals that arise due to the presence
at 2.36 and 2.08 ppm related to aromatic of neighboring protons. Figure 37
and aliphatic 1H on sp3 CH3 groups. shows the signals appear with
Meanwhile, the 13C-NMR analysis are varying multiplicities, indicating the
similar to L1 and L2 ligand but show peak presence of multiple protons in
that appears at 21.0 ppm indicating the neighboring C atoms.
3) Step 3: Identify the signal integration
presence of methyl carbon in the
value. Figure 37 shows several
aromatic ring while L1 and L2 do not show
proton integrations, ranging from
a peak for sp3 methyl carbon in the 1H, 2H, and 3H.
aromatic ring. Thus, if the 1H-NMR and 4) Step 4: Identify the peaks based on
13C-NMR analysis shown in Figures 34
the chemical shift value (δ). Based on
and 35 are combined, N-((3, 5-dimethyl- the reference data in Table 1, Figure
1H-pyrazol-1-yl)methyl)-4-methylpyridin 37 shows the similar result to L3
-2-amine compound is formed and its ligand 1H-NMR analysis. However,
structure is shown in Figure 36. Figure 37 shows a slightly different
chemical shift. The peak at 7.5 ppm
appear due to proton from amine
groups (N-H), peaks at 7.3 ppm as
well as 6.42 – 6.44 ppm appear due
to aromatic proton
1 2
( H on sp CH groups), peak at 5.73
ppm appear due to aliphatic protons
(1H on sp2 CH groups), peak at 5.40
appear due to 1H on sp3 CH2 groups
Figure 36 Structure of L3 ligand and bonded to electronegative
(Bouroumane et al., 2021) atoms, and peaks at 2.43 and 2.28
ppm appear due to aromatic and
aliphatic 1H on sp3 CH groups,
3
respectively.
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Figure 38 L4 ligand 13C-NMR spectrum (Bouroumane et al., 2021)
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4.4.4.2. 13C-NMR Spectra Analysis aromatic ring. Thus, if the 1H-NMR and
1) Step 1: Identify the number of 13C-NMR analysis shown in Figures 37
signals. Figure 38 shows twelve and 38 are combined, N-((3,5-dimethyl-

peaks appeared indicating the 1H-pyrazol-1-yl)methyl)-6-
existence of twelve types of carbon methylpyridin-2-amine compound is
atoms. formed and its structure is presented in
2) Step 2: Identify the chemical shift
Figure 39.
value (δ). Based on the reference
data in Table 2 and Figure 2, the
value of the carbon chemical shift
can be determined. Figure 38 shows
that the peaks similar to L3 ligand.
However, Figure 38 shows the peak
that represent C sp3 methyl appears
at higher chemical shift (24.4 ppm)
probably due to different position at Figure 39 Structure of L4 ligand
aromatic ring. (Bouroumane et al., 2021)
Based on the 1H-NMR and 13C-NMR 5. CONCLUSION

spectrum analysis in Figures 37 and 38, This study shows the simplest way to
respectively, the 1H-NMR analysis shows understand the results of 1H-NMR and
13C-NMR spectroscopic analysis. This
the signal appears as seven peaks : triplet
peak at 7.5 ppm related to proton from study was conducted by describing the
amine groups (N-H), triplet peak at 7.3 step-by-step how to read and interpret
1H-NMR and 13C-NMR spectra of several
ppm related to aromatic proton
(1H on sp2 CH groups), doublet peak at organic compounds based on the level of
6.42 – 6.44 ppm related to difficulty: (1) simple compounds, (2) fairly
1H on sp2 CH groups, singlet peak at 5.73 complex compounds, (3) more complex
ppm related to aliphatic protons compounds, and (4) very complex
(1H on sp2 CH groups), doublet peak at compounds. With this paper, we believe
5.44 ppm related to 1H on sp3 CH2 groups that this paper can be used as a basis for
and bonded to electronegative atoms, understanding and interpreting 1H-NMR
and singlet peaks at 2.43 and 2.28 ppm and 13C-NMR data.
related to aromatic and aliphatic
1H on sp3 CH groups,
6. AUTHORS’ NOTE
3 respectively. Authors declare that there is no
13
Meanwhile, the C-NMR analysis are conflict of interest regarding the
similar to L3 but show peak that appears publication of this article. Authors
at greater chemical shift (24,4) ppm for confirmed that the paper was free of
methyl carbon in the aromatic ring plagiarism.
probably due to different position at
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How To Read and Interpret 1H-NMR and 13C-NMR

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267

Indonesian Journal of Science & Technology 6 (2) (2021) 267-298

Indonesian Journal of Science & Technology

How to Read and Interpret 1H-NMR and 13C-NMR

ABSTRACTS ARTICLE INFO

© 2021 Tim Pengembang Jurnal UPI

1. INTRODUCTION levodopa compounds using 1H-NMR

in a different chemical environment thus giving the effect of magnetic field

Figure 1. Chemical shift (δ) of the 1H-NMR spectra

Figure 2. Chemical shift (δ) 13C-NMR spectra

Table 1. Chemical shift 1H-NMR

Type of Bond Chemical shift (δ) (ppm) Description

2 – 2.3 CH α – carbonyl (C=O)

2.3 Benzylic (C-Ph)

ROH 0.5 – 5 Alcohol

RNH2 0.5 – 5 Amine

Figure 3. Coupling constant value (J)

Table 2 Chemical shift 13C-NMR

100 – 150 165 – 175

110 – 170 205 – 220

3) Step 3: The structure of an organic 4. RESULTS AND DISCUSSION

compound. obtain information regarding the number

by-step exposure in determining simple

Figure 6. Methane 1H-NMR Spectra

Figure 7 Methane 13C-NMR spectra

4.1.1.1. 1H-NMR Spectra Analysis 2) Step 2: Identify the multiplicity of

Figure 8 Methanol 1H-NMR Spectra

Figure 9 Methanol 13C-NMR Spectra

electronegative OH group. Thus, if the 1H- 9 are combined, a CH3OH (methanol)

Figure 10 Acetylene 1H-NMR Spectra

Figure 11 Acetylene 13C-NMR Spectra

Based on the 1H-NMR and 13C-NMR 2) Step 2: Identify the multiplicity of

Figure 13 n-octane 1H-NMR Spectra (https://www.chemicalbook.com/SpectrumEN_111-

Figure 14 n-octane 13C-NMR Spectra (https://www.chemicalbook.com/SpectrumEN_111-

Figure 16 Isobutane 1H-NMR Spectra (Abraham & Mobli, 2008)

Figure 17 Isobutane 13C-NMR Spectra

Signal is not split by coupling as all 1H

Figure 19 Benzene 1H-NMR Spectra

Figure 20 Benzene 13C-NMR Spectra

Figure 22 Naphthalene 1H-NMR Spectra

Figure 23 Naphthalene 13C-NMR Spectra

4.2.2.2. 13C-NMR Spectra Analysis 1) Step 1: Identify the number of signals

Figure 25 Eugenol 1H-NMR spectrum analysis (Thirukumaran et al., 2014)

Figure 26 Eugenol 13C-NMR spectrum analysis (Thirukumaran et al., 2014)

4.3.1.2. 13C-NMR Spectra Analysis carbon chemical shift can be

Based on the 1H-NMR and 13C-NMR of neighboring protons. Figure 28

Figure 27 Structure of eugenol 4.4.1.2. 13C-NMR Spectra Analysis

Figure 28 L1 ligand 1H-NMR spectra (Bouroumane et al., 2021)

Figure 29 L1 ligand 13C-NMR spectra (Bouroumane et al., 2021)

Figure 31 L2 ligand 1H-NMR spectrum analysis (Bouroumane et al., 2021)

Figure 32 L2 ligand 13C-NMR spectrum analysis (Bouroumane et al., 2021)

Figure 33 Structure of L2 ligand 4.4.3.2. 13C-NMR Spectra Analysis

Figure 34 L3 ligand 1H-NMR spectra (Bouroumane et al., 2021)

Figure 35 L3 ligand 13C-NMR spectrum (Bouroumane et al., 2021)

Based on the 1H-NMR and 13C-NMR 4.4.4. NMR Spectra of N-((3,5-

Figure 37 L4 ligand 1H-NMR spectra (Bouroumane et al., 2021)

Figure 38 L4 ligand 13C-NMR spectrum (Bouroumane et al., 2021)

signals. Figure 38 shows twelve and 38 are combined, N-((3,5-dimethyl-

Based on the 1H-NMR and 13C-NMR 5. CONCLUSION