Synthesis, X-ray crystallography, vibrational spectroscopy, thermal and DFT studies of (E)-6-(4-methylstyryl)-4,5-dihydropyridazin-3(2H)-one

Article abstract of DOI:10.1016/j.molstruc.2020.129180

A novel pyridazin-3(2H)-one derivative, (E)-6-(4-methylstyryl)-4,5-dihydropyridazin-3(2H)-one (3) has been synthesized and characterized by FT-IR, UV–vis, ¹H- and ¹³C NMR, TGA/DTA thermal analysis and single-crystal X-ray diffraction. Furthermore, the molecular geometry, vibrational frequencies, electronic absorption spectra, chemical shift values, HOMO-LUMO analysis, frontier molecular orbital (FMO) and molecular electrostatic potential (MEP) surface map of the title compound were calculated using DFT/B3LYP method with 6–31+G (d,p) basis set. A comparison among the experimental and calculated results indicates that the vibrational frequencies, maximum electronic absorption wavelengths and chemical shift values are in a good agreement with each other. The intermolecular interactions in the crystal structure were investigated using Hirshfeld surface analysis. TGA/DTA thermal analysis revealed that the title compound is thermostable to its melting point.

Full text of DOI:10.1016/j.molstruc.2020.129180

Journal of Molecular Structure 1225 (2021) 129180
Contents lists available at ScienceDirect
Journal of Molecular Structure
journal homepage: www.elsevier.com/locate/molstr
Synthesis, X-ray crystallography, vibrational spectroscopy, thermal and
DFT studies of (E)-6-(4-methylstyryl)-4,5-dihydropyridazin-3(2H)-one
a
b
c
a
d
Said Daoui , Cemile Baydere , Feride Akman , Fouad El Kalai , Lhassane Mahi ,
b
e
f,∗
a
Necmi Dege , Yıldıray Topcu , Khalid Karrouchi , Noureddine Benchat
a
Laboratory of Applied Chemistry and Environment (LCAE), Faculty of Sciences, Mohammed I University, 60000 Oujda, Morocco
Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun, Turkey
b
c
University of Bingöl, Vocational School of Technical Sciences, 12000 Bingöl, Turkey
d
Moroccan Foundation for Advanced Science, Innovation and Research (Mascir). Department of Nanotechnology. Rabat Design Center, Rue Mohamed Al
Jazouli – Madinat Al Irfane Rabat 10 100, Morocco
e
Ondokuz Mayıs University, Faculty of Engineering, Chemical Engineering Department, Samsun, Turkey
f
Laboratory of Analytical Chemistry and Bromatology, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco
a r t i c l e i n f o
a b s t r a c t
Article history:
A novel pyridazin-3(2H)-one derivative, (E)-6-(4-methylstyryl)-4,5-dihydropyridazin-3(2H)-one (3) has
Received 7 June 2020
Revised 27 August 2020
Accepted 30 August 2020
Available online 31 August 2020
been synthesized and characterized by FT-IR, UV–vis, 1H- and 13 C NMR, TGA/DTA thermal analysis
and single-crystal X-ray diffraction. Furthermore, the molecular geometry, vibrational frequencies, elec-
tronic absorption spectra, chemical shift values, HOMO-LUMO analysis, frontier molecular orbital (FMO)
and molecular electrostatic potential (MEP) surface map of the title compound were calculated using
DFT/B3LYP method with 6–31+G (d,p) basis set. A comparison among the experimental and calculated
results indicates that the vibrational frequencies, maximum electronic absorption wavelengths and chem-
ical shift values are in a good agreement with each other. The intermolecular interactions in the crystal
structure were investigated using Hirshfeld surface analysis. TGA/DTA thermal analysis revealed that the
title compound is thermostable to its melting point.
Keywords:
Synthesis
Pyridazin-3(2h)-one
Crystal structure DFT Hirshfeld surface
Thermal analysis
©
2020 Elsevier B.V. All rights reserved.
1
. Introduction
of great support in identifying all species in any medium, espe-
cially when these studies are combined with theoretical calcula-
tions derived from the functional density theory (DFT) [14–22].
In continuation of our studies towards the molecular struc-
tures, Hirshfeld surfaces analysis and DFT studies of new pyridazin-
3(2H)-one derivatives [23–26], we report herein the synthe-
sis of new crystalline derivative i.e., (E)−6-(4-methylstyryl)−4,5-
dihydropyridazin-3(2H)-one (3) and, then it was characterized by
using FT-IR spectrum in the solid phase, UV–vis, 1H- and 13C NMR
spectra in DMSO–d6 solution, and single-crystal X-ray diffraction
(XRD) (Scheme 1). These experimental studies were accomplished
with theoretical DFT calculations by using the functional hybrid
B3LYP together with the 6–31+G(d,p) basis set in order to predict
the structural, electronic, optical and vibrational properties in the
gas phase. Hence, the intermolecular interactions were investigated
using Hirshfeld surface analysis and two-dimensional fingerprint
plots were also performed. Molecular orbital calculations providing
electron-density plots of HOMO and LUMO molecular orbitals and
molecular electrostatic potentials (MEP) were also computed both
with the DFT/B3LYP/6–31+G(d,p) basis set. In addition, the thermal
The synthesis of novel pyridazinone derivatives and inves-
tigation of their chemical and biological activities have gained
more importance in recent years [1,2]. Pyridazinone is an impor-
tant pharmacophore possessing the wide range of pharmacolog-
ical applications [3]. Literature survey revealed that substituted
pyridazinones have reported to possess biological activities such
as anti-HIV, antibacterial, anti-inflammatory, antidepressant, anti-
histaminic, antihypertensive, cardiotonic, anticonvulsant, acaracide
and herbicidal agents [4–13]. With this background set, the inves-
tigation of the structural, electronic and thermodynamic properties
of these pyridazin-3(2H)-one derivatives are important to know the
influence of different substituents on the structures in order to dis-
cover the relationship of these substituents with their pharmaco-
logical properties. On the other hand, spectroscopic studies and, in
particular, electron absorption spectra and vibrational assignments
of all the bands observed in the experimental infrared spectra are
∗
Corresponding author.
E-mail address: Khalid.karrouchi@um5s.net.ma (K. Karrouchi).
https://doi.org/10.1016/j.molstruc.2020.129180
0
022-2860/© 2020 Elsevier B.V. All rights reserved.

2
S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
Scheme 1. Synthesis of compound 3.
stability of the title compound was evaluated by TGA/DTA thermal
analysis.
2.3. X-ray crystallography
X-ray single-crystal diffraction for (3) was collected at 296 K
on a STOE IPDS II diffractometer equipped with an X-ray genera-
tor operating at 50 kV and 1 mA, using Cu-Kα radiation of wave-
2. Experimental section
˚
length 0.71073 A. The hemisphere of data was processed using
2
.1. General methods
SAINT [27]. The 3D structure was solved by direct methods and re-
fined by full-matrix least squares method on F2 using the SHELXL
program [28,29]. All the non-hydrogen atoms were revealed in the
first difference Fourier map and were refined with isotropic dis-
placement parameters. At the end of the refinement, the final dif-
ference Fourier map showed no peaks of chemical significance and
the final residual was 0.0641. The geometrical calculations were
carried out using the program PLATON [30]. The molecular and
packing diagrams were generated using Mercury for Windows [31].
Reactions were checked with TLC using aluminum sheets with
silica gel 60 F254 from Merck. Melting points were measured using
a Tottoli digital capillary melting point apparatus and are uncor-
rected. The FT-IR spectrum was recorded with Perkin-Elmer Parg-
amon 1000 PC FT-IR spectrometer over the range 400–4000 cm 1.
1H and 13C NMR spectra were recorded in DMSO–d6 solutions on
a Bruker Avance III spectrometer at 600 MHz for 1H NMR and
−
1
50 MHz for 13C NMR. The chemical shifts are expressed in parts
per million (ppm). TGA/DTA curves were recorded in a platinum
crucible in a pure air atmosphere at a flow rate of 20 mL/min and
over-temperature range 0–700 °C with a heating rate of 10 °C/min
using Shimadzu thermogravimetric analyzer DTG-60H.
2
.4. Computational details
DFT calculations were made using the Gaussian 09 package
program [32] and the results are shown using Gaussview 5.0
[
33] molecular visulation program. The applied method are Becke’s
34] three parameter hybrid exchange functional with Lee-Yang-
[
2
.2. Synthesis
Parr correlation functional [35] method (B3LYP) with 6–31+G (d,p)
basis set. The frequency calculations show that there is no imag-
inary frequency and optimized geometry has a true energy mini-
mum. FT-IR and NMR spectra in gas phase are determined by using
DFT method at B3LYP/6–31+G (d,p) level of theory and the detailed
vibrational assignments were calculated by means of the total en-
ergy distribution (TED) method using VEDA 4 program [36].
General procedure for the synthesis of (2): To a solution of
(
4 mmol, 0.46 g) of levulinic acid, (3 drops) of morpholine, (9
drops) of glacial acetic acid and in 20 ml of toluene was added
0.48 g, 4 mmol) of 4-methylbenzaldehyde (1). The reaction mix-
(
ture is brought to reflux for 12 h. The completion of the reaction
was monitored by TLC. After evaporation of the solvent under re-
duced pressure, the reaction mixture was cooled and washed with
a mixture of acetic acid: water (1: 4). In each case, the precipitate
formed was filtered and dried to give the compounds (2). Yellow
solid, Yield : 79%, m.p = 179–181 °C; 1H NMR (600 MHz, DMSO–
3. Results and discussion
3.1. Crystallography studies
d ) δ (ppm): 7.80 (d, J = 7.8 Hz, 2H, Ar), 7.61–7.55 (m, 3H, C=CH,
6
3
Ar), 6.82 (d, J = 16.3 Hz, 2H, C=CH), 2.91 (t, J = 9.0, 6.0 Hz, 2H,
A white coloured crystal of dimensions 0.38 × 0.34 × 0.31 mm
13
CH ), 2.34 (m, 5H, CH and CH ); C NMR (150 MHz, DMSO–d )
of compound 3 was chosen for an X-ray diffraction analysis. The
2
2
3
6
δ (ppm): 199.05 (C=O), 174.44 (COOH), 143.44 (CH=CH), 141.01 (C4
Ar), 131.96 (C4 Ar), 130.03 (CH=CH), 129.75 (C3 Ar), 129.52 (C2 Ar),
single crystal X-ray diffraction data show that it crystallizes in
monoclinic system, space group, P2 /n. The details of the crystal
1
3
5.22 (CH ), 28.29 (CH ), 21.41 (CH ).
data and structure refinement are given in Table 1. In the title
2
2
3
General procedure for the synthesis of (3): To a mixture of (0.22 g,
mmol) of compound (2) in 20 ml of ethanol is added (0.044 g,
compound (Fig. 1a), the dihydropyridazine ring is almost planar,
˚
1
having an r.m.s. deviation of 0.1737 A for the ring atoms, with the
˚
1.1 mmol) of hydrazine hydrate. The mixture is brought to re-
maximum deviation from the ring being 0.2684 (11) A for the C2
˚
flux for four hours. The precipitate was filtered, washed with wa-
ter, dried and recrystallized from ethanol. Single crystals were ob-
tained by slow evaporation at room temperature. White crystals,
Yield : 78%, m.p = 194–196 °C; FT-IR (ν(cm 1)) : 3305 (NH),
atom; the C3 atom lies −0.2565 (11) A in of the plane in the oppo-
site direction with the C2 atom. The benzene ring is close to planar
˚
with the r.m.s. deviation for the C7–C12 atoms being 0.0066 A [the
−
˚
maximum deviation from the least-squares plane is 0.0098 (12) A
905–2184 (CH), 1653 (C=O), 1604 (C=N), 1509, 1589 (C=C); 1H
2
for the C11 atom]. The dihedral angle between the two mentioned
planes is 12.102 (7)°, indicating an approximately planar relation-
ship. The O1=C1 bond length of the pyridazinone carbonyl func-
NMR (600 MHz, DMSO–d ) δ (ppm): 10.87 (s, 1H, NH), 7.48 (d,
6
J = 6.0 Hz, 2H, H-Ar), 7.19 (d, J = 6.0 Hz, 2H, H-Ar), 7.01 (d,
J = 18.0 Hz, 2H, C=CH), 6.84 (d, J = 18.0 Hz, 1H, CH=C), 2.77 (t,
J = 9.0, 6.0 Hz, 2H, CH ), 2.38 (t, J = 9.0, 6.0 Hz, 2H, CH ), 2.31 (s,
˚
tion is 1.2302 (17) A and the N1—N2 bond length in the dihydropy-
˚
ridazine ring is 1.3894 (17) A, both in accordance with values re-
2
2
13
3
H, CH ). C NMR (150 MHz, DMSO–d ) δ (ppm): 167.67 (C=O),
ported for related pyridazinones [37,38].
3
6
1
51.26 (C6 pyridazinone), 138.52 (C1 Ar), 133.82(C4 Ar), 133.80 (-
CH=CH-pyr), 129.89 (C3 Ar), 127.34 (C2 Ar), 125.87 (-CH=CH-pyr),
6.35 (C6 pyridazinone), 21.36 (C5 pyridazinone), 20.56 (CH ).
The main intermolecular interactions in the crystal structure of
the title compound are of type N—H…O, C—H•••π (Table 2). N1—
H1•••O1 hydrogen bonds between the NH function of the dihy-
2
3

S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
3
Table 1
Crystallographic and refinement data for compound (3).
CCDC Deposition Number
2,006,774
Chemical formula
C13H14N2O
Mr
214.26
Crystal system, space group
Monoclinic, P21/n
Temperature (K)
296
a, b, c ( A˚ )
7.4873 (5), 13.0255 (7), 12.1238 (8)
β (°)
V ( A˚ 3
107.108 (5)
1130.07 (13)
4
)
Z
Radiation type
Mo Kα
0.08
μ (mm 1)
−
Crystal size (mm)
0.38 × 0.34 × 0.31
Data collection
Diffractometer
STOE IPDS 2
Absorption correction
Integration (X-RED32; Stoe & Cie, 2002)
Tmin, Tmax
0.971, 0.990
7905, 2214, 1718
0.032
No. of measured, independent and observed [I > 2σ(I)] reflections
Rint
sin θ/λ)max ( A˚ 1)
−
(
0.617
Refinement
R[F2 > 2σ(F )], wR(F ), S
2
2
0.043, 0.114, 1.04
No. of reflections
2214
No. of parameters
147
H-atom treatment
H-atom parameters constrained
max, ꢀρmin (e A˚ 3)
−
ꢀρ
0.14, −0.14
dropyridazine ring and the carbonyl O atom generate centrosym-
2
2
metric dimers with an R (8) ring motif. The two types of hydro-
gen bonding results in the formation of layers parallel (200). In
the crystal, adjacent molecules are linked via C2—H2B•••Cg2 (3/2-
x, 1/2 + y, 1/2-z; Cg2 is the centroid of the C7–C12 benzene ring)
interactions, forming chains along [030] (Table 2, Fig. 2). Notable
π
•••π interactions are not observed.
3
.2. Optimized geometry
The optimized geometry of (E)−6-(4-methylstyryl)−4,5-
dihydropyridazin-3(2H)-one (3) is presented in Fig. 1b. The
optimized geometrical parameters of (E)−6-(4-methylstyryl)−4,5-
dihydropyridazin-3(2H)-one (3) in gas phase by using the B3LYP/6–
3
1+G (d,p) method are summarized in Table 3. These geometrical
parameters are compared in the same table with the corre-
sponding experimental ones determined. The deviation values are
also included in that table to evaluate the differences between
theoretical and experimental results. Hence, good correlations
are observed for bond lengths and angles with deviation values
˚
between 0 and 0.001 A for bond lengths and of 0 and 0.05° for
bond angles. The higher deviations are clearly observed for bond
angles H1—N1—C1 and H1—N1—N2 with deviation values 3.42
and 3.96°, respectively. The good correlations evidenced in the
bond lengths and angles, indicate that the optimized structure
of compound (3) in gas phase by using the B3LYP/6–31+G (d,p)
method can be used to perform the vibrational analysis.
From the results we can say that, the DFT/B3LYP functional
method estimated the bond lengths, bond angles and dihedral an-
gles in good agreement with literature [39–43].
Fig. 1. The molecular structure of the title compound: a) ORTEP drawn at the 50%
probability level. b) Optimized DFT/6–31+G (d,p) level.
3
.3. FT-IR study
The experimental and theoretical FT-IR spectra of the title com-
Table 2
Hydrogen-bond geometry ( A˚ , °).
pound are presented in Fig. 3. All vibrational assignments calcu-
lated by means of TED and the selected significant frequency vi-
brations are listed in Table 4.
D—H•••A
D—H
H•••A
D•••A
D—H•••A
N1—H1•••O1i
C2—H2B•••Cg2
0. 872 (19)
0. 97
2.026 (19)
2.72
2.8928 (17)
3.6598 (17)
172.6 (16)
162.0
ii
3
.3.1. N–H vibrations
Symmetry codes: (i) –x + 1,- y,- z + 1; (ii) –x + 3/2, y + 1/2,- z + 1/2
The N–H stretching vibrations are generally appears in the re-
gion 3500–3000 cm 1 [44]. This absorption is highly influenced
−

4
S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
Fig. 2. A view along the a axis of the crystal structure of the title compound. Blue dashed lines symbolize intermolecular N—H•••O hydrogen bonds; C—H•••π interactions
are shown as green dashes lines.
Table 3
Experimental and theoretical bond lengths and angles for compound (3). The crystallographic atom-labeling scheme was
followed.
XRD
DFT
ꢀ(Theor-Exp)
XRD
DFT
ꢀ(Theor-Exp)
Bond length ( A˚ )
Bond length ( A˚ )
O1-C1
1.230(2)
1.342(2)
1.390(2)
0.872(2)
1.286(2)
1.391(2)
1.392(2)
1.463(2)
1.327(2)
0.930
1.230
1.342
1.389
0.860
1.287
1.391
1.391
1.462
1.327
0.929
1.450
1.493
1.490
1.381
0.930
1.378
0
C10-C11
C10-C13
C5-H5
1.382(2)
1.506(2)
0.930
1.382
1.506
0.930
1.515
0.970
0.969
0.970
0.970
1.374
0.930
0.930
0.930
0.960
0.960
0.960
0
N1-C1
0
0
N1-N2
−0.001
−0.012
0.001
0
0
N1-H1
C2-C3
1.516(2)
0.970
−0.001
N2-C4
C2-H2A
C2-H2B
C3-H3A
C3-H3B
C12-C11
C12-H12
C11-H11
C9-H9
0
C7-C8
0.970
−0.001
C7-C12
−0.001
−0.001
0
0.970
0
0
0
0
0
0
0
0
0
C7-C6
0.970
C6-C5
1.374(2)
0.930
C6-H6
−0.0001
−0.001
−0.001
0
C4-C5
1.451(2)
1.494(2)
1.490(2)
1.382(2)
0.930
0.930
C4-C3
0.930
C1-C2
C13-H13A
C13-H13B
C13-H13C
0.960
C8-C9
−0.001
0
0.960
C8-H8
0.960
C10-C9
1.379(2)
−0.001
Bond angle (°)
N2-N1-C1
H1-N1-C1
H1-N1-N2
N1-N2-C4
C8-C7-C12
C6-C7-C8
C6-C7-C12
C7-C6-C5
H6-C6-C5
C7-C6-H6
N2-C4-C5
N2-C4-C3
C5-C4-C3
O1-C1-N1
O1-C1-C2
N1-C1-C2
C7-C8-C9
H8-C8-C9
C7-C8-H8
C11-C10-C9
C9-C10-C13
C11-C10-C13
C6-C5-C4
C6-C5-H5
C4-C5-H5
C1-C2-C3
Bond angle (°)
C1-C2-H2A
126.81
120.00
112.60
116.66
116.79
119.58
123.64
126.54
116.70
116.70
115.26
122.40
122.30
121.35
123.73
114.92
121.77
119.10
119.10
117.58
121.39
121.03
126.07
117.00
117.00
111.18
126.85
116.58
116.56
116.66
116.77
119.56
123.65
126.52
116.73
116.74
115.22
122.39
122.34
121.35
123.74
114.88
121.76
119.11
119.11
117.57
121.39
121.03
126.03
116.98
116.98
111.17
0.04
−3.42
3.96
0
109.40
109.40
109.40
109.40
108.00
110.33
109.60
109.60
109.60
109.60
108.10
121.07
119.50
119.50
121.86
119.10
119.10
120.91
119.50
119.50
109.50
109.50
109.50
109.50
109.50
109.50
109.39
109.39
109.40
109.40
108.01
110.36
109.57
109.57
109.58
109.58
108.11
121.08
119.45
119.45
121.84
119.07
119.08
120.91
119.54
119.54
109.46
109.46
109.46
109.47
109.47
109.47
−0.01
−0.01
0
H2A-C2-C3
C1-C2-H2B
H2B-C2-C3
0
−0.02
−0.02
0.01
−0.02
0.03
0.04
−0.04
−0.01
0.04
0
H2A-C2-H2B
C4-C3-C2
0.01
0.03
C4-C3-H3A
−0.03
−0.03
−0.02
−0.02
0.01
C2-C3-H3A
C4-C3-H3B
C2-C3-H3B
H3A-C3-H3B
C7-C12-C11
H12-C12-C11
C7-C12-H12
C10-C11-C12
C12-C11-H11
C10-C11-H11
C8-C9-C10
0.01
−0.05
−0.05
−0.02
−0.03
−0.02
0
0.01
−0.04
−0.01
0.01
0.01
−0.01
0
C10-C9-H9
0.04
C8-C9-H9
0.04
C10-C13-H13A
C10-C13-H13B
H13A-C13-H13B
C10-C13-H13C
H13A-H13-H13C
H13B-C13-H13C
−0.04
−0.04
−0.04
−0.03
−0.03
−0.03
0
−0.04
−0.02
−0.02
−0.01

S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
5
Table 4
Calculated frequencies, relative intensities, observed IR frequencies, and probable assignments of the compound (3).
DFT /B3LYP (cm 1
−
)
ν
Assignments, TED
DFT /B3LYP (cm
−1
)
ν
(cm
Assignments, TED
(IR)
(IR)
−1
)
−
ν
(
(DFT)
−
(cm 1)
(<10%)
ν
(cm
(DFT)
−1
(<10%)
cm 1
)
IIR
)
IIR
3
622.4
48.29
3305
νNH (100)
70.46
1256
δHCC (16) + δCCN (13)
νCC (16)
1
270.31
1
2
1
3.14
4.04
4.22
νCH (11) + νCH (84)
νCH (42) + νCH (55)
νCH (45)
44.79
4.44
3
3
3
3
198.52
190.66
177.05
173.6
1239.61
1235.43
1209.23
3184
νCC (36)
21.07
1210
δHCC (14) + δHCC
(18) + δHCC
(
21) + δHCC (13)
9.84
νCH (45)
21.95
23.71
33.39
4.81
1183
1153
δHCC (22) + δHCC
(14) + τHCCC (12)
νNN (23)
1
173.19
1
7
7
1
1
6.98
νCH (73)
3
3
3
3
171.05
166.97
128.57
120.14
1148.64
1142.83
1061.07
1040.63
.88
νCH (47) + νCH (40)
νCH (93)
δHCC (13)
.93
1107
1041
δHCH (10) + τHCCC
(24)
8.40
4.13
νCH (80)
1.79
τCNNC (14) + τCCNC
(21)
νCH (93)
3.76
δCCC (20)
3
3
097.17
087.8
1032.39
1013.2
15.52
3083
3045
νCH (52)
νCH (88)
32.05
5.73
1017
τHCCC (24)
1
4
1
7
1
1
1
1
2
1
7
9
8
1
1
0
1
1
2
2
2
2
5.44
5.60
1.15
66.68
09.48
8.46
3.20
3.83
4.99
1.02
.27
δHCH (12) + τHCCC
(30)
3
3
3
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
041.57
034.08
014.41
764.39
699.33
659.45
621.89
604.03
549.97
498.42
490.25
481.31
469.57
453.35
448.38
420.79
400.96
369.01
354.11
343.97
338.27
308.37
1009.19
1003.8
2920
2905
1653
νCH (47) + νCH (18)+
νCH (35)
12.46
0.01
995
973
δCCN (19) + δNNC
(18)+ τHCCN (11)
τHCCC (31)
νCH (91)
977.26
967.39
961.27
896.56
886.57
842.81
821.29
795.32
765.04
717.65
655.47
607.2
νOC (82)
69.67
1.01
νCC (15) + δNNC (11)
τHCCC (17)
νCC (40) + δHCC (14)
νCC (28)
960
1.35
δCCN (14) + δCCN (10)
τNCCC (13)
1604
νNC (41) + νCC (40)
νCC (18)
0.25
0.23
τHCCC (21)+ τHCCC
(25)+ τHCCC (27)
τHCCC (18)+ τHCCC
(18)+ τHCCC (15)
νNC (13) + νCC
(32) + δCCN (12)
δCCC (16)
1582
1509
δHCC (16) + δHCC (17)
49.61
4.13
δHCH (17) + δHCH
(17)
799
750
707
625
590
550
517
498
470
457
424
δHCH (41)
2.55
.45
δHCH (74) + δHCH
(13)
1.09
τCCCC (14)
.34
δHCH (73)
1.71
δCCC (17)+ δCCC (20)
τHNNC (23)
3.26
4.93
.06
1452
δHNN (54)
30.98
34.55
14.23
9.86
νCC (16) + δHNN (16)
590.5
τHNNC (20)+ τHCCN
(11) + τCNNC (10)
δOCN (15)+ τCCCC
(12)
δHCH (45) + δHCH
(25) + δHCH (22)
518.87
501.58
476.88
449.92
418.1
.57
1379
1351
νCC (15) + δHCC (17)
δOCN (12)+ τCCCC
(12)
10.41
.05
δHCC (21)
33.93
8.04
δCCC (11)
νCC (19) + δHCC (30)
νCC (12)
δOCN (23) + δCCC (17)
8.58
6.92
16.41
0.94
τCCCC (23) + τCCCC
(12)
δHCC (10) + τHCCC
(18) + τHCCN (19)
δHCC (22)
410.94
5.01
δOCN (11)+ τHCCN
(12)
1291
ν;stretching. δ; bending. τ; torsion vibrations.

6
S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
-
CH3 substituent group connected to benzene ring. Experimentally,
the series of IR bands in the range 3184–2905 cm 1 were assigned
as CH (sp2 and sp ) stretching modes of the 4-methylbenzyl and
pyridazin-3(2H)-one rings.
−
3
In para substituted benzene, the C–H in-plane bending or de-
−1
formations vibrations are observed in the region 1400–1000 cm
and are usually of medium to weak intensity [44,48–50]. Here,
some bands due to C–H in-plane bending vibration in the ti-
tle compound interact somewhat with other vibrations and they
can be assigned to the bands in the region between 1414 and
1
041 cm 1. The DFT calculations give these modes in the range
−
549–1142 cm 1
−
.
1
The out-of-plane C–H deformations are observed between 900
and 600 cm 1 [48–50]. Generally the CH out-of-plane deforma-
−
tions typical for para substituted benzenes are assigned in the
40 ± 50 cm 1 region [51]. In the present work, these vibra-
−
8
tion modes can be associated to the IR bands observed between
9
8
95 and 707 cm 1, experimentally and at 1009, 977, 961, 842 and
−
21 cm 1, theoretically.
−
3
.3.3. Carbonyl C=O vibrations
The stretching mode C=O is generally one of the most in-
tense peak in an infrared spectrum, it appears in a region 1800–
1
600 cm 1 [44]. For pyridazin-3(2H)-one, this mode was reported
−
at 1674 cm 1 by Bahçeli et al. [46] and at 1664 cm
−
−1
by Soliman
et al. [47]. In our study, the C=O stretching mode in the pyridazin-
−1
3
(2H)-one is assigned to the intense band at 1653 cm . This mode
was computed at 1764 cm 1
−
.
3
.3.4. C=N and N–N vibrations
Dede et al. [52] reported the C=N stretching vibrations at
−1
1616 cm
in pyridazin-3(2H)-one. For the title compound, the
bands observed at 1604 cm 1 are assigned as C=N stretching
−
−1
mode, which is comparable to theoretical value at 1621 cm . On
the other hand, the N–N stretching mode has been reported at
Fig. 3. Comparative representations of FT-IR spectra for (3).
1
131 cm 1 in bromopyrazone [53]. In the present case, the band
−
observed at 1153 cm 1 is assigned as N–N stretching vibration in
−
pyridazin-3(2H)-one, which is found to be in good agreement with
by chemical environment, mainly when NH group are involved
in hydrogen bonding. This can occur within the same molecule
the calculated value 1148 cm 1
−
.
(
intramolecular H bonding) or with neighboring molecules (inter-
3.3.5. C=C and C–C vibrations
molecular H bonding) [45]. The NH stretching band in pyridazin-
The aromatic C=C stretching vibrations of vinyl and phenyl ring
(2H)-one is reported at 3337 cm 1 by Bahçeli et al. [46] and at
−
−1
are very much important and occur in the region 1200–1650 cm
3
by Soliman et al. [47]. In the IR spectrum of 3, we observed a
sharp band of weak intensity at 3305 cm 1, assigned to νNH ab-
[48–50,53]. For the studied molecule, the calculated bands at 1699
−
−1
and 1659 cm
attributed to C=C stretching vibration in vinyl
sorption and the calculated value is 3622 cm 1. The difference
−
group and benzene ring, respectively. These vibration modes were
observed at 1509 and 1582 cm 1, experimentally. Moreover, the
−
observed between theoretical and experimental values concerning
νNH is due to the fact that the N1—H1•••O1 hydrogen bond was
not taken into account in our calculations: intermolecular H bonds
were purposely omitted since it is usually employed, for computa-
tion, a single molecule (gas phase) approach. Soliman et al. [47] re-
ported the N–H in-plane and out-of-plane deformation vibrations
i
C–C in plane and out of plane bending vibrations are reported at
673 and 580 cm 1, respectively [54]. The in-plane and out-of-plane
−
ring deformations of title compound are observed in the region be-
low 750 and 470 cm 1
−
.
in pyridazin-3(2H)-one at 1393 and 652 cm 1, respectively. In this
−
3.4. 1H and 13 C NMR chemical shifts
−
1
case, the bands observed at 1379 and 590 cm in IR spectrum are
The experimental and the theoretical 1H and 13C NMR chemical
shifts of the title compound were obtained by using DMSO–d6 as
solvent. The predicted ones were obtained at B3LYP/6–31+G(d,p)
level using CPCM model and GIAO method and the obtained results
and experimental values were given in Table 5. The proton NMR
spectrum of compound 3 displayed a singlet at δ = 2.31 ppm due
assigned as these modes. These deformation vibrations are calcu-
lated at 1453 and 607 cm 1, respectively.
−
3
.3.2. C–H vibrations
The C–H stretching vibrations of aromatic rings give rise to
−1
bands in the region 3200–3000 cm
in aromatic compounds
[
44,48–50]. Here, the calculated stretching vibrations in the range
to H28, H29 and H30 protons of methyl (CH ) group. Their corre-
3
of 3198–3166 cm 1 are attributed to C–H stretching vibration
−
sponding ones are underestimated by 2.93, 2.33 and 2.83 ppm. The
chemical shifts of H16, H17, H19 and H20 protons of methylene
in benzene ring. The scaled signals at 3128, 3097, 3041 and
014 cm 1 are attributed to the C–H (sp2 and sp ) stretching vi-
−
3
3
(-CH -) group of pyridazione appear as two triplets at δ = 2.38
2
brations in pyridazin-3(2H)-one ring and the signals at 3120, 3087
and 2.77 ppm. The chemical shifts of H7 and H14 protons of
and 3034 cm 1 are attributed to the stretching vibrations of the
−
vinyl (-CH=CH-) group appear as two doublets at δ = 6.84 and

S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
7
Table 5
The experimental and computed 1H- and 13 C NMR chemical shifts, all values in ppm of the
compound 3.
Atoms
Chemical shifts of hydrogen atoms
Atoms
Chemical shifts of carbon atoms
Exp.
Theo.
Exp.
Theo.
3
1
7
2
2
2
1
2
2
1
3
1
1
2
-H
10.87
7.48
7.01
7.19
7.19
7.48
6.84
2.38
2.31
2.38
2.31
2.77
2.77
2.31
8.39
8.24
8.02
7.67
7.58
7.54
7.04
3.08
2.93
2.85
2.83
2.74
2.52
2.33
9-C
167.67
151.21
133.82
138.52
127.34
125.87
129.89
129.89
127.34
133.80
21.36
153.99
139.36
128.25
120.33
118.79
118.55
116.27
116.01
109.70
108.06
20.04
1-H
-H
8-C
12-C
5-C
6-H
4-H
2-H
4-H
0-H
8-H
9-H
0-H
7-H
6-H
9-H
21-C
6-C
23-C
25-C
10-C
13-C
18-C
15-C
27-C
26.35
19.81
20.56
12.09
Fig. 4. Experimental (a) and simulated (b) UV–vis spectrum of the compound 3.
7.01 ppm. Indeed, the predicted chemical shifts of these protons
3.5. UV–vis analysis
are obtained at δ = 8.02 and 7.04 ppm, respectively. These chem-
ical shifts are relatively well reproduced with deviations less than
The experimental UV–vis absorption spectrum of the title com-
pound was recorded in methanol in the range 200 – 500 nm at
25 °C and has shown in Fig. 4a. The absorption spectrum of (3)
is characterized by a longer wavelength band with a maximum
around λ = 324 nm. The longer wavelength band can be attributed
1.01 ppm for H7 and 0.2 ppm for H14 compared to the observed
ones. The chemical shifts of the aromatic protons (H11, H22, H24
and H26) appeared as two doublets at δ = 7.19 and 7.48 ppm.
These chemical shifts are relatively well reproduced with devi-
ations less than 0.76 ppm compared to the observed ones. The
chemical shifts of the NH protons of pyridazinone appeared as sin-
glet at δ = 10.87 ppm. Their corresponding one are predicted at
δ = 8.39 ppm.
∗
to the n → π electronic transition resulting from the involved
molecular orbitals of the carbonyl (C=O) and the conjugated π
bond of aromatic system [55]. TD–DFT calculations at the B3LYP/6–
31+G(d,p) level were performed to obtain information about the
excited states and absorption characteristics. The longest wave-
length absorption maximum for the title compound is observed in
the UV region at λ = 318 nm as shown in Fig. 4b. The absorption
The carbon NMR spectrum showed the chemical shifts of C9
of carbonyl (C=O) at δ = 167.67 ppm. Their corresponding one
is obtained at δ = 153.99 ppm. The signals at δ = 151.26, 21.36
and 26.35 ppm are clearly assigned for C23, C21 and C5 carbons
of pyridazinone ring. Their corresponding ones are relatively well
reproduced with deviations of 13.88, 9.07 and 13.88 ppm, respec-
tively. The signals at δ = 133.80 and 125.87 ppm are assigned for
C6 and C13 carbons of vinyl (CH=CH) group. These protons are
predicted at δ = 118.55 and 108.06 ppm, respectively. The aromat-
ics carbon chemical shifts of the title compound occurred in the
range of 138.52–127.34 ppm. The signals at δ = 20.56 ppm are as-
∗
maximum is assigned to the n → π transitions that arise from
the carbonyl group (C=O) the conjugated π bond of styryl group
of the title compound. The strong cut–off wavelength for the study
is 350 nm (Fig. 5b) with an energy band gap of 3.546 eV. The cal-
culated electronic transition (318 nm) is in agreement with the ex-
perimental electronic transition observed (324 nm).
3
.6. Surfaces studies
signed for methyl (CH ) group and their corresponding one is ob-
3
tained at 12.09 ppm. Generally, the observed and calculated 1H and
13C NMR chemical shifts are in a very good agreement.
3.6.1. Hirshfeld surface analysis
Hirshfeld surface analysis was used to quantify the inter-
molecular contacts of the title compounds, using the software

8
S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
Fig. 5. (a) dnorm mapped on the Hirshfeld surface for visualing the intermolecular interactions, (b) shape-index map of the title compound and (c) curvedness map of the
title compound using a range from –4 to 4 A˚ .
Fig. 6. The Hirshfeld surface representations with the function dnorm plotted onto the surface for (a) H•••H, (b) H•••C/ C•••H, (c) H•••O/O•••H, (d) H•••N/N•••H
interactions.
Table 6
Crystal-Explorer17.5 [56]. The Hirshfeld surface were planned us-
Calculated frontier molecular orbital energies (eV) for 3.
ing a standart (high) surface resolution with the three-dimensional
dnorm surfaces plotted over a fixed color scale of −0.5573 (red)
to 1.3718 (blue) a.u. The Hirshfeld surfaces of the title com-
pound were mapped over dnorm, shape index and curvedness
Fig. 5a-c. The Hirshfeld surface representations with the func-
tion dnorm plotted onto the surface are shown for the H•••H,
H•••C/C•••H, H•••O/O•••H, H•••N/N•••H, C•••N/N•••C, C•••C in-
FMO
Energy
E(HOMO)
−6.0709
−1.9986
4.0723
2.0361
0.4911
4.0347
E(LUMO)
ꢀE (HOMO–LUMO)
Hardness, η
Softness, σ
Electronegativity, χ
teractions in Fig. 6a-f, respectively. The overall two-dimensional
fingerprint plot and those delineated into H•••H, H•••C/C•••H,
H•••O/O•••H, H•••N/N•••H, C•••N/N•••C, C•••C contacts are il-
lustrated in Fig. 7a–g, respectively. The largest interaction is H•••H
regions indicate the strongest attraction regions, which are occu-
pied mostly by hydrogen atoms.
contributing 52.5% to the overall crystal packing. The peak in the
˚
•••
O/O H contacts makes 14.6% con-
•••
center de = di = 1.15 A. H
tribution to the Hirshfeld surface. The contacts is represented by
˚
a pair of sharp spikes in the region de + di ~1.85 A in the finger-
3.7. Frontier molecular orbital analyses
print plot. H•••O/O•••H interactions arises from the intermolecu-
lar N—H•••O hydrogen bonding (Table 2) and H•••O/O•••H con-
The energy levels for the title compound were computed by
theoretically via density functional theory (DFT) using the standard
B3LYP functional and 6–31+G(d,p) basis-set calculations [34] as
implemented in GAUSSIAN 09 [32]. The HOMO (highest occupied
molecular orbital) acts as an electron donor and the LUMO (low-
est occupied molecular orbital) as an electron acceptor. When the
energy gap is small, the molecule is highly polarizable and has
high chemical reactivity. The energy levels, energy gaps, hardness
(η), softness (σ) and electronegativity (χ) are given in Table 6.
The electron transition from the HOMO to the LUMO energy
level is shown in Fig. 9. The chemical hardness and softness of
a molecule is a sign of its chemical stability. From the HOMO–
LUMO energy gap, we can see whether or not the molecule is
hard or soft. If the energy gap is large, the molecule is hard and
if small the molecule is soft. Soft molecules are more polariz-
able than hard ones because they need less energy for excita-
tion. Therefore from Table 6 we conclude that the title molecule
tacts. The contributions of the other contact to the Hirshfeld sur-
face is H•••C/C•••H (19.7%), H•••N/N•••H (8.3%), C•••N/N•••C
(
2.5%), C•••C (2.5%).
3
.6.2. Molecular electrostatic potentials
Molecular electrostatic potential (MEP) displays molecular size
and shape as well as positive, negative and neutral electrostatic
potential regions in terms of color grading and is useful in in-
vestigating relationships between molecular structure and physico-
chemical properties [57,58]. The MEP map (Fig. 8) was calculated at
the B3LYP/6–31+G (d,p) level of theory. The red and blue-coloured
regions indicate nucleophiles (electron rich), and electrophile re-
gions (electron poor), respectively. The white regions indicate neu-
tral atoms. In the title molecule, the red regions are concentrated
at the carbonyl group. It possesses the most negative potential and
is thus the strongest repulsion site (electrophilic attack). The blue

S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
9
Fig. 7. The full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H•••H, (c) H•••C/ C•••H, (d) H•••O/O•••H,
e) H•••N/N•••H interactions.
(
Fig. 8. Molecular electrostatic potential surface of 3 in B3LYP/6–31+G (d,p).
Fig. 9. Molecular orbital energy levels of the title compound.

10
S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
Fig. 10. TGA, DrTGA and DTA curves of compound (3).
belongs to the hard materials with a HOMO–LUMO energy gap
of 4.0723 eV.
Declaration of Competing Interest
The authors declare that they have no known competing finan-
cial interests or personal relationships that could have appeared to
influence the work reported in this paper.
3
.8. TGA/DTA thermal analysis
To study the behavior of the sample material against temper-
ature, differential thermal analysis (DTA) and thermogravimetric
CRediT authorship contribution statement
analysis (TGA) of the compound (3) in the temperature range from
5
0 to 700 °C with a heating rate of 10 °C min 1, were studied.
−
Said Daoui: Methodology, Investigation. Cemile Baydere: Con-
ceptualization, Methodology. Feride Akman: Software, Writing
Fig. 10 shows the TGA, DrTGA, and DTA curves of compound 3.
The TGA curve of the compound shows two stages of decomposi-
-
review & editing. Fouad El Kalai: Investigation, Resources.
◦
tion. The title compound is stable up to 117 C and then begins
Lhassane Mahi: Investigation, Resources. Necmi Dege: Validation.
Yıldıray Topcu: Investigation, Resources. Khalid Karrouchi: Con-
ceptualization, Writing - original draft, Writing - review & editing.
Noureddine Benchat: Supervision.
to decompose. In the first step of decomposition, the weight loss
◦
of 4.067% occurs in the temperature range 117–190 C. In the sec-
ond step of decomposition, the weight loss of 86.82% occurs in the
◦
temperature range 190–366 C. The decomposition is completed
◦
◦
around 560 C. In the DTA curve the endothermic peak at 210
C
Acknowledgement
indicates the melting point of the title compound.
This work is supported by Mohammed
I University of
4. Conclusion
Oujda and Ondokuz Mayıs University (award project No.
PYO.FEN.1906.19.001). Feride Akman would like to thank Bingöl
University for the server and Bitlis Eren University for Gaussian
software.
A
novel
pyridazin-3(2H)-one
derivative,
(E)−6-(4-
methylstyryl)−4,5-dihydropyridazin-3(2H)-one (3) has been
synthesized and characterized by FT-IR, UV–vis, 1H- and 13C NMR,
and single-crystal X-ray diffraction. The electronic structure, FT-IR
vibrational frequencies, electronic absorption spectra, chemical
shift values have been calculated at DFT/B3LYP with 6–31+G
Supplementary materials
(
d,p) basis set. FT-IR spectral analysis indicates that the calculated
Supplementary material associated with this article can be
found, in the online version, at doi:10.1016/j.molstruc.2020.129180.
vibrational frequencies satisfactorily agree with the experimentally
assigned values. The TD-DFT calculations lead to a very closer
agreement with the experimental absorption spectra. Hirshfeld
and MEP surface analyses provide the information concerning the
region from where the compound can have intermolecular inter-
actions. The thermal behavior and stability of the title compound
were analyzed by using TGA and DTA techniques which revealed
that the compound is thermostable up to its melting point.
References
[1] S. Dubey, P.A. Bhosle, Pyridazinone: an important element of pharmacophore
possessing broad spectrum of activity, Med. Chem. Res. 24 (2015) 3579–3598.
[
2] W. Akhtar, M. Shaquiquzzaman, M. Akhter, G. Verma, M.F. Khan, M.M. Alam,
The therapeutic journey of pyridazinone, Eur. J. Med. Chem. 123 (2016)
256–281.

S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
11
[
[
[
[
3] M. Asif, A mini review on biological activities of pyridazinone derivatives as
antiulcer, antisecretory, antihistamine and particularly against histamine H3R,
Mini-Rev. Med. Chem. 14 (2014) 1093–1103.
[27] Bruker, APEX3, SAINT, SADABS & SHELXTL, Bruker AXS, Inc., Madison, WI, 2016.
[28] G.M. Sheldrick, Crystallographic Shelves: Space-Group Hierarchy Explained,
Acta Cryst. A71 (2015) 3–8.
[29] G.M. Sheldrick, Crystal structure refinement with SHELXL, Acta Cryst. C71
(2015) 3–8.
[30] A.L. Spek, Structure validation in chemical crystallography, Acta Crystallograph-
ica Section D: Biological Crystallography 65 (2) (2009) 148–155.
[31] C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock,
L. Rodriguez-Monge, R. Taylor, J. van de Streek, P.A. Wood, Mercury CSD 2.0
- new features for the visualization and investigation of crystal structures, J.
Appl. Cryst. 41 (2008) 466–470.
4] M.A. El-Hashash, D.B. Guirguis, N.A.M. AbdEl-Wahed, M.A. Kadhim, Synthe-
sis of novel series of phthalazine derivatives with antibacterial and antifungal
evaluation, J. Chem. Eng. Process Technol. 5 (2014) 1000191–1000196.
5] A.A. Siddiqui, R. Mishra, M. Shaharyar, A. Husain, M. Rashid, P. Pal, Triazole
incorporated pyridazinones as a new class of antihypertensive agents: design,
synthesis and in vivo screening, Bioorg. Med. Chem. Lett. 21 (2011) 1023–1026.
6] Y. Boukharsa, B. Meddah, R.Y. Tiendrebeogo, A. Ibrahimi, J. Taoufik, Y. Cher-
rah, M.E.A. Faouzi, Synthesis and antidepressant activity of 5-(benzo [b] fu-
ran-2-ylmethyl)-6-methylpyridazin-3 (2H)-one derivatives, Med. Chem. Res. 25
[32] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheese-
man, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Car-
icato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg,
M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Naka-
jima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Per-
alta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov,
T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant,
S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox,
J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann,
O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Mo-
rokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich,
A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian
09, Revision C.01, Gaussian, Inc., Wallingford CT, 2010.
(2016) 494–500.
[
[
[
7] D.G.H. Livermore, R.C. Bethell, N. Cammack, A.P. Hancock, M.M. Hann,
D.V.S. Green, R.B. Lamont, S.A. Noble, D.C. Orr, J. Med. Chem. 36 (1993)
3784–3794.
8] C. Barberot, A. Moniot, I. Allart-Simon, L. Malleret, T. Yegorova, M. Laronze–
Cochard, J. Sapi, Synthesis and biological evaluation of pyridazinone derivatives
as potential anti-inflammatory agents, Eur. J. Med. Chem. 146 (2018) 139–146.
9] S. Partap, M.J. Akhtar, M.S. Yar, M.Z. Hassan, A.A. Siddiqui, Pyridazinone hy-
brids: design, synthesis and evaluation as potential anticonvulsant agents,
Bioorg. Chem. 77 (2018) 74–83.
[
10] T. Wang, Y. Dong, L.C. Wang, B.R. Xiang, Z. Chen, L.B. Qu. Design, syn-
thesis and structure-activity relationship studies of 6-phenyl-4, 5-dihydro-3
(
2H)-pyridazinone derivatives as cardiotonic agents, Arzneimittelforschung 58
2008) 569–573.
[33] R. Dennington, T. Keith, J. Millam, GaussView, Version 5, Semichem Inc.,
Shawnee Mission KS, 2010.
(
[
11] M. Tao, L.D. Aimone, J.A. Gruner, J.R. Mathiasen, Z. Huang, J. Lyons, R.L. Hud-
kins, Synthesis and structure–activity relationship of 5-pyridazin-3-one phe-
noxypiperidines as potent, selective histamine H3 receptor inverse agonists,
Bioorg. Med. Chem. Lett. 22 (2012) 1073–1077.
[34] A.D. Becke, Density-functional exchange-energy approximation with correct
asymptotic behavior, Phys. Rev. A. 38 (1988) 3098.
[35] C. Lee, W. Yang, R.G. Parr, Development of the Colle-Salvetti correlation-energy
formula into a functional of the electron density, Phys. Rev B. 37 (1988) 785.
[36] M.H. Jamroz, Vibrational Energy Distribution Analysis VEDA 4, Warsaw, 2004.
[37] Stoe & Cie, X-AREA and X-RED32, Stoe & Cie GmbH, Darmstadt, Germany,
2002.
[
12] M.A. Dekeyser, Acaricide mode of action, Pestic. Sci. 61 (2005) 103–110.
13] M.Antifeedant Asif, herbicidal and molluscicidal activities of pyridazinone
compounds, Mini-Rev. Org. Chem. 10 (2013) 113–122.
[
[
[
[
[
14] O. Noureddine, S. Gatfaoui, S.A. Brandán, H. Marouani, N. Issaoui, Struc-
[38] S. Abourichaa, N. Benchat, A. Anaflous, A. Melhaoui, T. Ben-Hadda, B. Oussaid,
M. Bolte, 6-Phenyl-4, 5-dihydropyridazin-3 (2H)-one, Acta Cryst. E59 (2003)
o802–o803.
tural, docking and spectroscopic studies of
-Phenylpiperazine-1,4-diium-bis (hydrogen sulfate), J. Mol. Struct. 1202
2020) 127351.
a new piperazine derivative,
1
(
[39] S. Dadou, S. Kansiz, S. Daoui, F. El Kalai, C. Baydere, R. Saddik, K. Kar-
rouchi, N. Dege, N. Benchat, Crystal structures and Hirshfeld surface analy-
ses of 4-benzyl-6-phenyl-4, 5-dihydropyridazin-3 (2H)-one and methyl 2-[5-(2,
6-dichlorobenzyl)-6-oxo-3-phenyl-1, 4, 5, 6-tetrahydropyridazin-1-yl] acetate,
Acta Cryst. E75 (2019) 1679–1684.
15] K. Karrouchi, E. Yousfi, N. Sebbar, Y. Ramli, J. Taoufik, Y. Ouzidan, M. Ansar,
Y. Mabkhot, H. Ghabbour, S. Radi, New Pyrazole-Hydrazone Derivatives: x-ray
Analysis, Molecular Structure Investigation via Density Functional Theory (DFT)
and Their High In-Situ Catecholase Activity, Int J Mol Sci. 18 (2017) 2215.
16] M.A. Iramain, M.V. Castillo, L. Davies, E. María, M.E. Manzur, S.A. Brandán,
Structural and SQMFF study of potent insecticide 4,4-DDT combining the
FT-IR and FT-Raman spectra with DFT calculations, J. Mol. Struct. 1199 (2020)
[40] S. Daoui, E.B. Çınar, F. El Kalai, R. Saddik, N. Dege, K. Karrouchi, N. Ben-
chat, Crystal structure, Hirshfeld surface analysis and DFT studies of
6-[(E)-2-(thiophen-2-yl) ethenyl]-4, 5-dihydropyridazin-3 (2H)-one, Acta Cryst.
E75 (2019) 1880–1883.
[41] S. Daoui, C. Baydere, F. El Kalai, R. Saddik, N. Dege, K. Karrouchi,
N. Benchat, Crystal structure and Hirshfeld surface analysis of
(E)-6-(4-hydroxy-3-methoxystyryl)-4, 5-dihydropyridazin-3 (2H)-one, Acta
Cryst. E75 (2019) 1734–1737.
[42] M.A.M. El-Mansy, M.S. El-Bana, S.S. Fouad, On the spectroscopic analyses of
3-Hydroxy-1-Phenyl-Pyridazin-6 (2H) one (HPHP): a comparative experimental
and computational study, Spectrochim. Acta A. 176 (2017) 99–105.
[43] S. Bahçeli, H. Gökce, A Study on Spectroscopic and Quantum Chemical Calcu-
lations of Levosimendan, Indian. J. Pure. Ap. Phy. 52 (2014) 224–235.
[44] D.W. Mayo, F.A. Miller, R.W. Hannah, Course Notes On the Interpretation of
Infrared and Raman spectra, John Wiley & Sons, 2004.
[45] K. Karrouchi, S. Fettach, M.M. Jotani, A. Sagaama, S. Radi, H.A. Ghabbour,
Y.N. Mabkhot, B. Himmi, M.E.A. Faouzi, N. Issaoui, Synthesis, crystal structure,
hirshfeld surface analysis, DFT calculations, anti-diabetic activity and molec-
ular docking studies of (E)-N’-(5-bromo-2-hydroxybenzylidene) isonicotinohy-
drazide, J. Mol. Struct. 1221 (2020) 128800.
126964.
17] R.R. Pillai, K. Karrouchi, S. Fettach, S. Armakovi c´ , S.J. Armakovi c´ , Y. Brik,
J. Taoufik, S. Radi, M.E.A. Faouzi, M. Ansar, Synthesis, spectroscopic charac-
terization, reactive properties by DFT calculations, molecular dynamics sim-
ulations and biological evaluation of Schiff bases tethered 1, 2, 4-triazole and
pyrazole rings, J. Mol. Struct. 1177 (2019) 47–54.
[
18] S. Tighadouini, R. Benabbes, M. Tillard, D. Eddike, K. Haboubi, K. Kar-
rouchi, S. Radi, Synthesis, crystal structure, DFT studies and bio-
logical activity of (Z)-3-(3-bromophenyl)-1-(1, 5-dimethyl-1 H-pyra-
zol-3-yl)-3-hydroxyprop-2-en-1-one, Chem. Cent. J. 12 (1) (2018) 122.
[
19] O. Noureddine, S. Gatfaoui, S.A. Brandan, A. Sagaama, H. Marouani, N. Issaoui,
Experimental and DFT studies on the molecular structure, spectroscopic prop-
erties, and molecular docking of 4-phenylpiperazine-1-ium dihydrogen phos-
phate, J Mol. Struct. 1207 (2020) 127762.
[
20] K. Karrouchi, S.A. Brandán, Y. Sert, H. El-marzouqi, S. Radi, M. Ferbin-
teanu, M.E.A. Faouzi, Y. Garcia, M. Ansar, Synthesis, X-ray structure, Vi-
brational spectroscopy, DFT investigation and biological evaluation studies of
(
E)-N’-(4-(dimethylamino)benzylidene)-5-methyl-1H-pyrazole-3-carbohydrazide,
[46] S. Bahçeli, H. Gökce, A Study on Spectroscopic and Quantum Chemical Calcu-
lations of Levosimendan, Indian. J. Pure. Ap. Phy. 52 (2014) 224–235.
[47] S.M. Soliman, J. Albering, M.A. Abu-Youssef, Molecular structure, spectro-
scopic properties, NLO, HOMO–LUMO and NBO analyses of 6-hydroxy-3
(2H)-pyridazinone, Spectrochim. Acta A. 136 (2015) 1086–1098.
J. Mol. Struct. 1219 (2020) 128541.
[
21] Y. Bouzian, K. Karrouchi, Y. Sert, C.H. Lai, L. Mahi, N.H. Ahabchane, A. Tal-
baoui, J.T. Mague, E.M. Essassi, Synthesis, spectroscopic characterization, crystal
structure, DFT, molecular docking and in vitro antibacterial potential of novel
quinoline derivatives, J. Mol. Struct. 1209 (2020) 127940.
[48] O. Noureddine, S. Gatfaoui, S.A. Brandán, H. Marouani, N. Issaoui, Struc-
tural, docking and spectroscopic studies of a new piperazine derivative,
[
22] R.A. Rudyk, M.A. Checa, C.A.N. Catalán, S.A. Brandán, F.T.-.I.R. Structural, FT-Ra-
man and ECD studies on the free base, cationic and hydrobromide species of
scopolamine alkaloid, J Mol. Struct. 1180 (2019) 603–617.
1-Phenylpiperazine-1,4-diium-bis (hydrogen sulfate), J Mol. Struct. 1202 (2020)
127351.
[
23] S. Daoui, C. Baydere, T. Chelfi, F. El Kalai, N. Dege, K. Karrouchi, N. Ben-
chat, Polymorphism of 2-(5-benzyl-6-oxo-3-phenyl-1, 6-dihydropyridazin-1-yl)
acetic acid with two monoclinic modifications: crystal structures and Hirshfeld
surface analyses, Acta Cryst. E76 (2020) 432–437.
[49] S. Gatfaoui, N. Issaoui, S.A. Brandán, T. Roisnel, H. Marouani, Synthesis and
characterization of p-xylylenediaminiumbis(nitrate). Effects of the coordination
modes of nitrate groups on their structural and vibrational properties, J. Mol.
Struct. 1151 (2018) 152–168.
[
[
[
24] S. Daoui, E.B. Cinar, F. El Kalai, R. Saddik, K. Karrouchi, N. Benchat,
C. Baydere, N. Dege, Crystal structure and Hirshfeld surface analysis of
[50] O. Noureddine, S. Gatfaoui, S.A. Brandan, A. Sagaama, H. Marouani, N. Issaoui,
Experimental and DFT studies on the molecular structure, spectroscopic prop-
erties, and molecular docking of 4-phenylpiperazine-1-ium dihydrogen phos-
phate, J Mol. Struct. 1207 (2020) 127762.
4-(4-methylbenzyl)-6-phenylpyridazin-3 (2H)-one, Acta Cryst. E75 (2019)
1352–1356.
25] S. Daoui, M.S.H. Faizi, F.E. Kalai, R. Saddik, N. Dege, K. Karrouchi,
N. Benchat, Crystal structure and the DFT and MEP study of 4-ben-
zyl-2-[2-(4-fluorophenyl)-2-oxoethyl]-6-phenylpyridazin-3 (2H)-one, Acta Cryst.
E75 (2019) 1030–1034.
26] S. Daoui, C. Baydere, F. El Kalai, L. Mahi, N. Dege, K. Karrouchi, N. Ben-
chat, Crystal structure, Hirshfeld surface analysis and DFT studies of
[51] S.R. Sheeja, N.A. Mangalam, M.P. Kurup, Y.S. Mary, K. Raju, H.T. Varghese,
C.Y. Panicker, Vibrational spectroscopic studies and computational study of
quinoline-2-carbaldehyde benzoyl hydrazone, J. Mol. Struct. 973 (2010) 36–46.
[52] B.
Dede,
D.
Avcı,
S.
Bahçeli,
Study
on
the
4-ethoxy-2-methyl-5-(4-morpholinyl)-3 (2H)-pyridazinone using FT-IR, 1H
and 13 C NMR, UV-vis spectroscopy, and DFT/HSEH1PBE method, Can. J. Phys.
96 (9) (2018) 1042–1052.
2-[5-(4-methylbenzyl)-6-oxo-3-phenyl-1, 6-dihydropyridazin-1-yl] acetic acid,
Acta Cryst. E75 (2019) 1925–1929.

12
S. Daoui, C. Baydere and F. Akman et al. / Journal of Molecular Structure 1225 (2021) 129180
[
53] H. Gökce, S. Bahçeli, Spectroscopic and quantum chemical studies on bromopy-
[56] M.J. Turner, J.J. McKinnon, S.K. Wolff, D.J. Grimwood, P.R. Spackman, D. Jayati-
laka, M.A. Spackman, CrystalExplorer17, University of Western Australia, 2017
http://hirshfeldsurface.net.
razone, Spectrochim Acta A 133 (2014) 741–751.
[
54] M.A.M. El-Mansy, M.S. El-Bana, S.S. Fouad, On the spectroscopic analyses of
3
-Hydroxy-1-Phenyl-Pyridazin-6 (2H) one (HPHP): a comparative experimental
[57] J.S. Murray, K. Sen, Molecular Electrostatic potentials: Concepts and Applica-
tions, Elsevier, 1996.
[58] E. Scrocco, J. Tomasi, Advances in Quantum Chemistry, Academic Press, New
York, 1978.
and computational study, Spectrochim. Acta A. 176 (2017) 99–105.
55] M. Pokharia, S.K. Yadav, H. Mishra, N. Pandey, R. Tilak, S. Pokharia, Synthe-
sis, spectroscopic characterization, biological activity and theoretical studies
of (E)-N3-(2-chlorobenzylidene)-H-1, 2, 4-triazole-3, 5-diamine, J. Mol. Struct.
[
1144 (2017) 324–337.