Investigation of Spectroscopic and Electronic Properties of 2-
Hydroxyacetophenone Methanesulfonylhydrazone By Dft Method
HAMİT ALYAR1, SALİHA ALYAR2, IMAD ALİ TALAB3
1,3Department of Physics,
Çankırı Karatekin University,
TÜRKİYE
2Department of Chemistry,
Çankırı Karatekin University,
TÜRKİYE
Abstract: - Sulfonamides are broad-spectrum antibacterial chemicals that work against gram-positive and gram-
negative bacteria. Sulfonamides were widely employed soon after their discovery, and this resulted in a large
reduction in bacterial illnesses. In this study, firstly we performed geometrical optimization. After this,
investigated spectroscopic (such as 1H-NMR, 13C-NMR and FT-IR) and electronic properties of 2-
hydroxyacetophenone methanesulfonylhydrazone by theoretically. As a result of the vibrational frequencies, 1H-
NMR and 13C-NMR calculations, it was seen that the theoretical values were compatible with the experimental
values. In addition, HOMO-LUMO molecular orbital energies, nonlinear optical (NLO) properties and molecular
electrostatic potential (MESP) of 2-hydroxyacetophenone methanesulfonylhydrazone compound were
investigated. As a result of calculations, the energy band gap between the HOMO and LUMO orbitals of the
studied compound was found 4.65 eV and first static hyperpolarizability was found as 4674.7×10-33 esu
(approximately 12.34 times larger than urea). All calculations were performed using DFT/B3LYP/6-311++G (d,
p) level of theory and Gaussian 09 and Gauss View 5.0 package programs.
Key-Words: -FT-IR, NMR, NLO, DFT, HOMO- LUMO, MESP
Received: March 19, 2024. Revised: August 11, 2024. Accepted: September 15, 2024. Published: November 29, 2024.
1 Introduction
Sulfonamides are among the most used antibiotics
in the world. It has been used clinically since 1968.
They have been applied in the treatment of infections,
especially urinary tract and upper respiratory tract
infections. Their low prices, low toxic effects and
superior efficacy against common bacterial diseases
have made them stand out. Between 1935 and 1948,
4500 sulfonamide derivatives were synthesized and
their antimicrobial activities were investigated.
However, only 0.5 percent of these compounds were
used as drugs. Sulfonamides are in the structure of
para amino benzene sulfonilamide and provide the
bacteriostatic effect of the amino benzene ring, which
is the active part [1].
Sulfonamides are antibacterial compounds has a
broad spectrum of antimicrobial activity against
Gram-positive and Gram-negative bacteria. The
majority of sulfonamide formulations are offered as
a combination of a sulfonamide and one of the
synthetic diaminopyrimidines, trimethoprim or
ormethoprim.
In addition to antibacterial and antitumor
properties, sulfonamides also have many
pharmacological properties such as anti-carbonic
anhydrase, diuretic, hypoglycemic antithyroid and
protease inhibitory activity. Examples of these are the
carbonic anhydrase inhibitor acetazolamide (in
clinical use for more than 45 years), widely used
diuretic furosemide, hypoglycemic agent torasemide,
anticancer sulfonamide E7070 used in further clinical
studies, HIV protease inhibitor used in the treatment
of HIV infection and AIDS amprenavir and
metalloprotease inhibitors can be given [2].
In this study, firstly, 2-hydroxyacetophenone
methanesulfonylhydrazone compound was
optimized and the minimum energy stable structure
was obtained. After obtaining the stable structure of
the molecule, vibration frequencies, 1H-NMR and
13C-NMR calculations were first performed on this
structure. Finally, we have studied HOMO and
LUMO molecular orbital energies, nonlinear optical
properties (NLO), electrostatic potential maps
(MESP) in the DFT/B3LYP/6-311++ G (d, p)
theoretical plane.
2 Materials and Methods
Molecular modeling and spectroscopic methods are
among the scientific research methods that are widely
used to examine the molecular behavior and
structural properties of chemical and biological
systems. In this study, spectroscopic and some
International Journal of Chemical Engineering and Materials
DOI: 10.37394/232031.2024.3.8
Hami
t Alyar, Sali
ha Alyar, Imad Ali
Talab
E-ISSN: 2945-0519
59
Volume 3, 2024
electronic properties of the 2-hydroxyacetophenone
methanesulfonylhydrazone molecule were
investigated theoretically by using DFT method.
First, we will optimize the structure of 2-
hydroxyacetophenone methanesulfonylhydrazone
compound synthesized by Saliha ALYAR [3]. The
lowest energy structure will be obtained by the
DFT/B3LYP/6-311++G (d, p) method. After
calculating the vibrational frequencies of this
compound, 1H and 13C NMR calculations will be
made in the DMSO phase and compared with the
experimental results. Finally, HOMO and LUMO
molecular orbital energies, nonlinear optical
properties (NLO) and molecular potential energy
surface (MESP) maps will be examined using the
DFT/B3LYP/6-311++G (d, p) basis set. Theoretical
results will be understood by comparing them to
experimental values. All theoretical calculations are
performed using two software packages Gaussian 09
and Gauss View 5.0 [4,5].
3. Results and Discussion
The conformation analysis of the 2-
hydroxyacetophenone methanesulfonylhydrazone
was performed by Alyar et al. and it was found to
have seven different conformations [6]. In the
conformation analysis study performed with the
B3LYP/ 6-31G** basis set, it was found that the most
stable conformer was found in the vacuo. In this
study, geometric optimization calculation was made
with the DFT B3LYP/6-311++G(d,p) basis set using
the lowest energy structure of these seven
conformations and its stable structure was found as
follows.
Figure 1. Optimize structure of 2-
Hydroxyacetophenone methanesulfonylhydrazone
3.1 Vibrational Assignment of 2-
Hydroxyacetophenone Methanesulfonylhydrazone
The marks of the fundamental vibration frequencies
determined for the stable structure of the 2-
hydroxyacetophenone methanesulfonylhydrazone
molecule at lowest energy were created and
interpreted in this portion of our study. 2-
hydroxyacetophenone methanesulfonylhydrazone is
a 27-atom compound having 75 fundamental
vibration frequencies. The experimental FT-IR
spectrum of the 2-hydroxyacetophenone
methanesulfonylhydrazone molecule is given in Fig.
2. The experimental and theoretical vibration
frequencies are listed in the Table 1.
Figure 2 Experimental FT-IR spectrum of 2-
hydroxyacetophenone methanesulfonylhydrazone
molecule [3]
In aromatic molecules, C-H stretching vibrations are
generally observed in the range of 3000-3100 cm-1,
in-plane and out-of-plane bending vibrations are
observed in the range of 1275-1000 cm-1 and 900-690
cm-1, respectively [7]. S. Alyar symmetric and
asymmetric stretching C-H vibrations observed at
3016 and 2971 cm-1 [3]. While the symmetric C-H
ring stretching vibrations were calculated at 3202, the
asymmetric C-H stretching vibrations calculated at
3186 and 3172 cm-1 for the 2-hydroxyacetophenone
methanesulfonylhydrazone by using the B3LYP/6-
311++G(d,p) method.
C-H ring vibration frequencies are higher than
CH2 and CH3 vibration frequencies. In aromatic ring
systems, the C-H stretching vibrations of the methyl
group, which can generally be called the electron
donating group, are expected to occur
asymmetrically at 2980 cm-1 and symmetrically at
2870 cm-1[8-10]. The CH3 asymmetric and
symmetric stretching vibrations observed at 2908,
2850 and 2820 cm-1 by S. Alyar [3]. In our study
symmetric and asymmetric CH3 stretching vibrations
calculated at 3177, 3165, 3152 and 3084 cm-1. The
symmetric CH3 stretching vibrations calculated at
3065 and 3024 cm-1.
International Journal of Chemical Engineering and Materials
DOI: 10.37394/232031.2024.3.8
Hami
t Alyar, Sali
ha Alyar, Imad Ali
Talab
E-ISSN: 2945-0519
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Table 1. Vibrational assignments of 2-
Hydroxyacetophenone Methanesulonylhydrazone by
DFT B3LYP/6-311++ G (d,p) level of theory
Mode
Exp.
[3]
Calculation
Assignment
75
3203
3495
ν (NH)
74
3420
ν (OH)
73
3016
3202
νs (CH)ring
72
2971
3194
νas (CH)ring
71
3186
νas (CH)ring
70
3177
νas (CH3)
69
3172
νas (CH)ring
68
2908
3165
νas (CH3)
67
2850
3152
νas (CH3)
66
3084
νas (CH3)
65
2820
3065
νs (CH3)
64
3026
νs (CH3)
63
1652
ν(CC)ring +
β (COH)
62
1622
1638
ν (N=C) +
ν(CC)ring
61
1573
1602
ν (N=C) +
ν(CC)ring +
β (COH)
60
1500
1526
ν(CC)ring +
β (CCH)ring
+ β (COH)
59
1500
β (CH3) + β
(CCH)ring
58
1451
1486
ν(CC)ring + ν
(CO) + β
(CCH)ring +
β (COH)
57
1483
β (C14H3)
56
1425
1448
β (C14H3)
55
1410
1443
β (C14H3)
54
1427
β (CCH)ring
+ β (COH)
+ β (N19H)
53
1409
β (CCH)ring
+ β (COH)
+ β (N19H)
+ γ (C14H3)
52
1389
1398
β (COH) +
β (N19H) +
γ (C14H3)
51
1370
1354
γ (C24H3)
50
1339
1350
ν(CC)ring +
ν(C4C13) +
ν(CN) + γ
(C14H3)
49
1332
ν(CC)ring +
ν(C3O) +
ν(C4C13)+
β (CCH)ring
48
1322
1303
νas (SO2) +
β (N19H)
47
1299
1275
ν(CC)ring +
ν(C3O) + β
(CCH)ring
46
1250
1245
ν(CC)ring +
β(C3OH) +
β (CCH)ring
45
1241
1183
β (CCH)ring
44
1172
1152
ν(CC)ring +
ν(NN) + β
(CCH)ring
43
1153
1122
s(SO2) +
ν(CC)ring +
ν(NN) + β
(CCH)ring
42
1097
185.5429
ν(CC)ring +
ν(NN) + β
(CCH)ring +
β (CCC)ring
41
1092
152.5505
ν(CC)ring +
β (CCH)ring
+ γ (C14H3)
40
1045
1054
40.7272
ν(CC)ring + γ
(C14H3)
39
1034
1047
22.8648
γ (C14H3)
38
999
27.2566
γ (C14H3)
37
993
0.6996
τ (CCCC)ring
+ τ
(CCCH)ring
36
984
169.4419
γ (C24H3)
35
978
4.3147
ν(C13C14)
+ γ (C14H3)
+ γ (C24H3)
34
963
3.1680
τ (CCCC)ring
+ τ
(CCCH)ring
33
840
882
151.7558
ν(SN) +
ν(C13C14)
+ γ (C14H3)
32
870
1.75
τ (CCCC)ring
+ τ
(CCCH)ring
31
778
845
11.3304
ν(CO) +
ν(SN) + β
(CCC)ring
30
766
79.2857
τ (CCCC)ring
+ τ
(CCCH)ring
+ τ
(CCCO)ring
29
746
753
7.0328
ν(SN) +
ν(C13C14)
+ β
(CCC)ring
28
732
193.8310
τ
(CCOH)ring
+ τ
(CCCC)ring
+ τ
(CCCH)ring
27
727
708
86.9478
ν(CS) +
ν(C13C14)
+ τ
(CCOH)ring
O – H stretching vibration generally gives a
strong band in the region of 3550 –3700 cm-1.
However, when there is an interaction between other
existing groups, the O – H stretching vibration shifts
to around 3200 cm-1. In this study, the O – H
stretching vibration were calculated at 3420 cm-1.
C - N stretching vibrations are experimentally
observed in the range of 1357 cm-1 –1313 cm-1 for
the 2Cl-5NBAK molecule. Theoretically, this
vibration was calculated in the ranges of 1403 cm-1 -
1378 cm-1 and 1364 cm-1 - 1354 cm-1 in HF and
B3LYP/6-311++G (d, p), respectively [11]. The C=N
stretching vibrations observed at 1622 and 1573 cm-1
by Alyar [3]. In this study, the C=N stretching
vibration was calculated at 1638 and 1602 cm-1.
In the FT-IR spectrum, the peak at 1322 cm-1
indicates the asymmetric sulfoxide (–SO2) group
stretching, and the peak at 1153 cm-1 indicates the
International Journal of Chemical Engineering and Materials
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symmetrical sulfoxide (–SO2) group stretching.
While asymmetric sulfoxide (–SO2) group stretching
vibration calculated at 1303 cm-1, the symmetrical
sulfoxide (–SO2) group stretching was calculated at
1122 cm-1.
3.2 NMR Results of 2-Hydroxyacetophenone
Methanesulfonylhydrazone
NMR analysis in molecular structures allows us to
have an idea about the number of carbon and
hydrogen atoms in the structure of the molecule.
NMR analysis of molecule 2-hydroxyacetophenone
methanesulfonylhydrazone was theoretically carried
out.
Experimental 1H-NMR and 13C-NMR values of 2-
hydroxyacetophenone methanesulfonylhydrazone
molecule have not been found in the literature.
Theoretical NMR calculations of the 2-
hydroxyacetophenone methanesulfonylhydrazone
molecule were made in the DFT/ B3LYP and GIAO
method on the base set 6-311++G(d,p). In Table 2,
the theoretically calculated 1H and 13C NMR
chemical shift values of 2-hydroxyacetophenone
methanesulfonylhydrazone molecule using DMSO
solution are listed.
In the structure of the 2-hydroxyacetophenone
methanesulfonylhydrazone molecule, hydrogen
atoms are located in the aromatic ring and the methyl
group. The (1H) NMR signals for the protons in the
aromatic ring were calculated at 7.34 (H7), 6.94(H8),
7.58(H9) and 6.93 (H10) ppm values.
Theoretical mean values of (1H) NMR chemical shift
was calculated as 2.24 and 3.96 ppm for C14H3 and
C24H3, respectively.
Chemical shifts of carbon atoms in molecules with
aromatic rings in their structure are usually obtained
at a value of 100-150 ppm [12,13]. Six of the carbon
atoms in the 2-hydroxyacetophenone
methanesulfonylhydrazone molecule are located in
the phenyl ring. Two other carbon atoms are located
in the CH3 functional groups. The 13C NMR chemical
shift values for (C1-C6) were found to be between
131.77-118.36 ppm theoretically.
Table 2. The experimental 1H and 13C- NMR
chemical shifts (ppm) together within the calculated
data for 2-hydroxyacetophenone
methanesulfonylhydrazone
Assignment
ẟ(calc)
C3
159.90
C13
157.44
C1
131.77
C5
129.09
C4
119.53
C6
118.36
C2
116.88
C24
43.30
C14
12.086
H12
10.68
H9
7.58
H7
7.34
H8
6.94
H10
6.93
H20
6.55
H27
6.35
H25
2.98
H26
2.56
H16
2.55
H15
2.10
H17
2.06
3.3 HOMO-LUMO Analyze
By looking at the electron density distribution of a
structure, information about the ionization potential,
electron affinity, chemical hardness and softness
parameters, electrostatic potential and molecular
orbital shapes can be obtained. Molecular orbitals are
called HOMO-LUMO. Here HOMO is the tendency
of the molecule to donate electrons, and the occupied
orbital is the highest energy. LUMO, on the other
hand, is the tendency of the molecule to gain
electrons and is the lowest vacant orbital [14]. When
the energy difference (ΔE) of the molecule is large,
the electron distribution undergoes less change and
the polarization is low. The distribution of frontier
orbitals can reveal information about a molecule's
reactivity and the active site. Figure 3 depicts the
HOMO-LUMO frontier orbital compositions for 2-
hydroxyacetophenone methanesulfonylhydrazone
computed using the DFT/6-311++G(d,p) levelof
theory. The energy difference between HOMO and
LUMO given in Figure 3 is 4.65 eV. Its large size
indicates that the molecule is stable and durable in
terms of thermodynamics. In addition, the molecule
does not react with itself, dimerization,
polymerization does not take place.
International Journal of Chemical Engineering and Materials
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Figure 3. The frontier molecular orbitals of the 2-
hydroxyacetophenone methanesulfonylhydrazone
3.4 Nonlinear Optical (NLO) Properties
Nonlinear optical materials have been of great
interest in recent years due to their potential
applications in the field of optoelectronics, namely
telecommunications, optical computing, optical data
storage, optical switching, and various photonic
technologies [15,16]. In organic materials, optical
properties are determined by polarizability. The
polarizability of an atom or molecule is a measure of
how easily the nucleus and electrons can be displaced
from their stable states. The easily displaced
electrons in an atom or molecule are the valence
electrons that are furthest from the nucleus.
Therefore, it has a great contribution to the
polarizability of valence electrons [17].
Although the method for estimating initial static
hyperpolarizability from Gaussian 09 data was
previously reported, it’s everything summed up here.
The output of Gaussian 09 yields ten components of
the equation 3 x 3 x 3 matrix as βxxx; βxxy; βxyy;
βyyy; βxxz; βxyz; βyyz; βxzz; βyzz; βzzz; from
which the x, y, and z components of are computed.
One popular technique for presenting the value of β
in a single form is to consider use the Equation (1) to
solve for the average of the three independent values
for as a quasi-pythagorean problem.
βtot = ( βx2 + βy2 + βz2 )1/2 ………….(1)
The following Equation (2) is the entire equation for
obtaining total first static hyperpolarizability from
Gaussian09 output:
βtot = [( βxxx + βxyy + βxzz )2 + ( βyyy + βyzz + βyxx
)2 + ( βzzz + βzxx + βzyy )2 ]1/2…………(2)
Because Gaussian 09’s β values are expressed in
atomic units (a.u.), the estimated βtotal values were
translated to electrostatic units (esu) (1 a.u. = 8.6393x
10-33 esu). In addition, the total dipole moment and
average polarizability of the compound were
calculated using the Equation (3) and Equation (4).
μ= 〖(μx2+ μy2+μz2)〗1/2 (3)
<α> = 1/3 (αxx+ αyy+ αzz ) (4)
Because of its characteristics in the research of
nonlinear optical properties, urea is regarded a
generic reference. The NLO characteristics of the
molecules under consideration are assessed by
comparing them to urea. Urea values acquired from
DFT/B3LYP/6-31G calculations (d), µ = 1.3732
Debye, α = 3.8312 Å3 and β = 0.37289*10-30 cm5/
esu. [18].
The computed electric dipole moment, polarizability,
and first-order hyperpolarizability properties of the
investigated substance are provided in Table 3.
Table 3. The electric dipole moment μ (D), the mean
polarizability <α> and the first hyperpolarizability
(βtot) of 2-hydroxyacetophenone
methanesulfonylhydrazone
Parameter
Parameter
µx
-1.1594
βxxx
-320.8
µy
1.2844
βxxy
164.1
µz
1.5800
βxyy
2.1
µtot
2.3431
βyyy
86.6
αxx
232.66
βxxz
71.2
αxy
3.09
βxyz
-37.5
αyy
154.32
βyyz
45.9
αxz
-4.30
βxzz
-80.8
αyz
3.11
βyzz
28.0
αzz
102.56
βzzz
118.6
<α>(a.u)
163.18 a.u
βtot (a.u)
541.1
<α>(esu)
24.18*10-24 (esu)
βtot(esu)
4674.7*10-
33esu
Table 3 shows the components of β as well as the
final βtotal values determined by Gaussian 09 for the
2-hydroxyacetophenone methanesulfonylhydrazone.
The studied compound has the greatest
hyperpolarizability value of 4674.7 x10-33 esu, which
is nearly 12.34 times larger than that of urea. We can
say that the studied compound present large
nonlinear optical activity and it can be used for
nonlinear optical applications.
International Journal of Chemical Engineering and Materials
DOI: 10.37394/232031.2024.3.8
Hami
t Alyar, Sali
ha Alyar, Imad Ali
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E-ISSN: 2945-0519
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3.5 Molecular Electrostatic Potential (MESP)
The interactions of molecules and atoms in the
molecule with each other are possible by determining
the electron density distribution (i.e. very dense and
less dense regions) in the molecule. MESP, or
“Molecular Electrostatic Potential” maps, give the
three-dimensional electrostatic potential shape of the
molecule surface. Electrostatic potential maps are
very useful for visualizing varying charge
distributions. The molecular electrostatic potential
(MESP) describes the interaction energy between the
unit positive charge and the molecular charge
distribution of the system. Negative regions of the
molecular potential energy surface are associated
with electrophilic reactivity (relative abundance of
electrons), positive ones with nucleophilic reactivity
[19].
The surface seen on the MESP map gives molecular
size and shape values as well as electrostatic
potential. In MESP maps, the regions indicated in red
represent the region with negative electron density,
while the regions indicated in blue and white are
represented by color codes to show regions with
positive charges in terms of electron density. The
interpretation of these maps is very important in
determining the location of the active regions of the
reactions that will take place in the molecule. The
color indicator chart shows a transition from blue to
red, and this color transition can be correlated with
electron density on the map [20]. Regions with low
electron density have high potential, while regions
with dense electrons have low potential. With the
calculation made in the gas environment, it is seen in
Figure 4 that the electron-rich regions are located on
the O22, O23 and O11 oxygen atoms attached to the
benzene ring at the SO2 end. The electron-poor
regions are on the hydrogen atoms attached to the
benzene ring and on the hydrogen atoms in the
methyl components.
Figure 4. MESP map of 2-hydroxyacetophenone
methanesulfonylhydrazone molecule
Considering the MESP map results support the N-
H…O bond for all methods. Thus, nucleophilic and
electrophilic regions were determined for the
molecule. In this case, it will allow us to foresee
where the reaction should be carried out in the new
molecules to be synthesized.
The DFT/B3LYP/6-311++G (d, p) level of theory
was used to construct molecular electrostatic
potential energy surfaces of 2-hydroxyacetophenone
methanesulfonylhydrazone compounds.
4 Conclusion
In this study, quantum chemical calculations of the
sulfonamide compound 2-hydroxyacetophenone
methanesulfonylhydrazone which was synthesized
by S. Alyar before, were made.
First, the minimum energy structure of this
compound, which has seven different conformations,
was selected and the structure was optimized using
the DFT B3LP/6-311++G (d, p) method. Then, using
the stable structure of the studied molecule, FT-IR,
1H-NMR and 13C-NMR calculations were performed,
vibration frequencies and chemical shift values were
analyzed. In the FT-IR study, it was seen that the
experimental and theoretical results were compatible
with each other.
Finally, the HOMO-LUMO molecular orbital
energies, nonlinear optical properties and molecular
potential energy surfaces of the studied compound
were investigated. As a result of the calculations, the
energy band gap of the studied compound was 4.65
eV and its hyperpolarizability was calculated as
4674.7x10-33 esu (approximately 12.34 times larger
than urea).
As a result of the calculations, it was determined that
the studied compound showed moderate nonlinear
optical properties.
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International Journal of Chemical Engineering and Materials
DOI: 10.37394/232031.2024.3.8
Hami
t Alyar, Sali
ha Alyar, Imad Ali
Talab
E-ISSN: 2945-0519
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Volume 3, 2024
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Contribution of Individual Authors to the
Creation of a Scientific Article (Ghostwriting
Policy)
Hamit ALYAR was responsible writing-review and
editing.
Imad Ali TALAB carried out the simulation and the
optimization.
Saliha ALYAR is responsible for the preparation of
the tables and the pictures.
Sources of Funding for Research Presented in a
Scientific Article or Scientific Article Itself
No funding was received for conducting this study.
Conflict of Interest
The authors have no conflicts of interest to declare
that are relevant to the content of this article.
Creative Commons Attribution License 4.0
(Attribution 4.0 International, CC BY 4.0)
This article is published under the terms of the
Creative Commons Attribution License 4.0
https://creativecommons.org/licenses/by/4.0/deed.en
_US
International Journal of Chemical Engineering and Materials
DOI: 10.37394/232031.2024.3.8
Hami
t Alyar, Sali
ha Alyar, Imad Ali
Talab
E-ISSN: 2945-0519
65
Volume 3, 2024