Synthesis, analytical and spectral characterization for new VO (II)-triazole complexes; conformational study beside MOE docking simulation features

Article abstract of DOI:10.1002/aoc.5505

New triazole-derivatives were synthesized and characterized (spectral, analytical and conformational). After that, the new derivatives were coordinated with VO (II) atom to prepare new series of complexes. Distorted octahedral and square-pyramidal geometries, were the geometries suggested based on UV- Vis and ESR spectra. A neutral poly-dentate mode of bonding was proposed by 1:1 (M:L), for all complexes. TGA study supports the molecular formula of VO (II) complexes as well as, mass spectral-analysis that executed for examples. The isotropic, anisotropic, molecular orbital and Hamiltonian parameters were estimated upon ESR spectra, for selected complexes. XRD patterns were executed for three complexes, two among appeared with particulate-sizes in nanometer-range. Conformational study was executed for all synthesizes applying RTD-B3LYP-FC method. Essential physical parameters were estimated and discussed. MOE-docking that considered a bright part, was performed over all compounds towards 3s7s and 5jm5, as functional tumor proteins. The docking interaction parameters, introduced strongly some synthesizes to be anti-tumor agents.

Full text of DOI:10.1002/aoc.5505

Received: 4 November 2019
DOI: 10.1002/aoc.5505
Revised: 10 December 2019
Accepted: 12 December 2019
F U L L P A P E R
Synthesis, analytical and spectral characterization for new
VO (II)-triazole complexes; conformational study beside
MOE docking simulation features
1,2
1,3
1,2
Nashwa El-Metwaly
| Thoraya A. Farghaly
| Marwa G. Elghalban
1
Chemistry Department, Faculty of
Applied Sciences, Umm Al-Qura
University, Makkah, Saudi Arabia
New triazole-derivatives were synthesized and characterized (spectral, analyti-
cal and conformational). After that, the new derivatives were coordinated with
VO (II) atom to prepare new series of complexes. Distorted octahedral and
square-pyramidal geometries, were the geometries suggested based on UV- Vis
and ESR spectra. A neutral poly-dentate mode of bonding was proposed by 1:1
(M:L), for all complexes. TGA study supports the molecular formula of VO
2
Chemistry Department Faculty of
Science, Mansoura University, Mansoura,
Egypt
3
Chemistry Department, Faculty of
Science, Cairo University, Giza, Egypt
(II) complexes as well as, mass spectral-analysis that executed for examples.
Correspondence
The isotropic, anisotropic, molecular orbital and Hamiltonian parameters were
estimated upon ESR spectra, for selected complexes. XRD patterns were exe-
cuted for three complexes, two among appeared with particulate-sizes in nano-
meter-range. Conformational study was executed for all synthesizes applying
RTD-B3LYP-FC method. Essential physical parameters were estimated and
discussed. MOE-docking that considered a bright part, was performed over all
compounds towards 3s7s and 5jm5, as functional tumor proteins. The docking
interaction parameters, introduced strongly some synthesizes to be anti-tumor
agents.
Prof. Nashwa M. El-Metwaly, Chemistry
Department Faculty of Science, Mansoura
University, Mansoura, Egypt.
Email: n_elmetwaly00@yahoo.com
Funding information
Deanship of Scientific Research at Umm
Al-Qura University, Grant/Award
Number: 17-SCI-1-03-0001
K E Y W O R D S
ESR, Modeling, MOE docking, new VO (II) complexes, TGA
1
| INTRODUCTION
with different transition metals revealed wide range of
potent implementations in various fields as medicinal,
agriculture, catalysis and insecticides. Moreover, multi-
dentate Schiff bases carrying 1,2,4-triazole ring metal-
[
6]
Muti-dentate ligands play a vital role in coordination
chemistry. They have contributed to the production of
numerous applied metal complexes in several fields such
[1]
complexes have received much attention due to their
[2]
[7–9]
as pharmaceutical and catalytic industries. NSO con-
tent ligands, served excellently as chelating agents
towards many atoms both transition and non-transition.
The ligands having nitrogen, oxygen and sulfur donor
atoms served as excellent chelating agents for both transi-
tion and non-transition metal ions as VO (II) ion. Coor-
dination chemistry field attracts scientists to enrich
studies, by offering new complexes have distinguish
versatile biological and catalytic applications.
Combi-
nation of the three moieties in one ligand will be created
a multi-dentate ligand with different types of coordina-
tion cores {NO or NS} as sketched in Figure 1. Inspired
our recent successful research project work concerned
with synthesis of bioactive heterocyclic-metal-
[3]
[
10–12]
complexes,
we aim to deepen the study around
vanadyl based on biological effectiveness of its com-
plexes, as mentioned. Here we choose triazole derivatives
[4,5]
applications.
Complexes of Schiff base or triazoles
Appl Organometal Chem. 2020;e5505.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5505

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EL-METWALY ET AL.
hydroxybenzaldehyde 2 (3.05 g, 0.025 mol) in glacial
acetic acid (20 ml) for 10 hr. Solid 2-(((3-mercapto-5-
(
trifluoromethyl)-4H-1,2,4-triazol-4-yl)imino)methyl)phe-
[
14]
nol 3 was isolated by filtration.
The second step repre-
sented in Schiff base 3 contribution (2.88 g, 0.01 mole) in
substitution reaction with hydrazonoyl chloride esters
4a-e (0.01 mol) in 20 ml ethanol. The mixture was
FIGURE 1 The different coordination cores of the new multi-
dentate ligands
refluxed for a long time (≈ 20 hr) after adjusting the
medium by adding 1.4 ml of Et N. After that, the purity
3
of medium was verified by TLC, then the solid trisubsti-
tuted-traizole derivatives were filtered off and re-crystal-
lized (ethanol/drops of dioxane). The chemical formulae
of tri-substituted-triazole ligands 5 have been demon-
strated based on analytical (Table 1) and spectral analysis
enriched with active ingredients that lead to distinctive
and stable complexes, which may serve excellent in many
fields. New synthesizes will be investigated by analytical
and spectral techniques to establish their most fitted
geometries. Also, the molecular modeling will be exe-
cuted by sophisticated program to extract important
physical parameters. Moreover, MOE-docking was exe-
cuted against two tumor cell-proteins, to give well expec-
tation for the biological feature of new compounds.
1
13
(Tables 2 & 3). IR and H & C NMR spectra (at,
850 MHz, Figures 2, 1S &2S) suggested the structural for-
mulae of aimed triazole derivatives. All functional signals
were assigned and aggregated (Tables 2 & 3), for exam-
1
ple, H NMR spectrum of 5b derivative (Figure 2) showed
six functional signals at δ (ppm) = 1.42 (t, CH ), 2.45 (s,
3
CH ), 4.45 (q, CH ), 7.77 (s, N=CH), 8.73(s, OH) and
3
2
2
| METHEDOLOGY
10.03 (s, NH) beside multiple signals for aromatic groups.
13
Also, C NMR spectrum (Figure 2) showed three ali-
phatic carbons at δ = 14.19, 21.25 and 63.21 ppm for two
CH and one CH In addition to counted aromatic car-
All chemicals, reagents and solvents were purchased
from Fluka, Merck & Sigma-Aldrich and used without
pre-treatment process.
3
2.
bons, other functional signals were appeared at
δ = 166.51, 158. 27 and 157.52 ppm that attribute to = C-
OH, carbonyl-ester and azomethene groups (HC=N).
3
3
| SYNTHESIS
.1 | Synthesis of tri-substituted-[1,2,4]
3.2 | Synthesis of VO (II)-trisubstituted-
triazole complexes
triazole derivatives (ligands 5a-e)
Five traizole derivatives 5a-e were synthesized
0.002 mol of each tri-substituted triazole derivative 5a-e,
were dissolved in ethanol (40 ml) under reflux till com-
plete dissolution. 0.004 mol of VOSO .xH O (0.704 g,
through two steps as illustrated in Scheme 1. The first
[13]
step was achieved
via refluxing mixture of
4
2
aminotriazolethiol derivative 1 (4.6 g, 0.025 mol) and 2-
without xH O) were dissolved in small amount of ethanol
2
SCHEME 1 Synthesis of ligands 5a-5e

EL-METWALY ET AL.
3 of 16
TABLE 1 Physical and analytical characteristics of triazole derivatives (5a-e) and their VO (II) complexes
Elemental analysis (%) Calcd (Found)
1
Compounds (Empirical
formula/Found)
Λ
m, Ohm−
cm mol
2
−1
Color
C
H
N
S (total)
SO
4
V
1
2
3
4
5
6
7
8
9
1
) (C21
508.47),5a-HTMoA
) [VO (HTMoA)](SO
671.48, VO (II)-5a)
)(C21 S)
492.47),5b-HTMeA
H
19
F
3
N
6
O
4
S)
--
Faint yellow
49.60(49.61)
3.77(3.75)
16.53(16.52)
6.31(6.34)
---
---
(
4
)
50.10
--
Olive green
37.56(37.55)
51.22(51.22)
37.45(37.44)
50.21(50.20)
36.43(36.44)
46.84(46.84)
33.74(33.73)
45.89(45.90)
33.25(33.27)
2.85(2.88)
3.89(3.87)
3.14(3.14)
3.58(3.60)
2.90(2.88)
3.14(3.13)
2.83(2.83)
3.08(3.07)
2.79(2.78)
12.52(12.50)
17.06(17.05)
12.48(12.49)
17.57(17.60)
12.74(12.72)
16.39(16.40)
11.80(11.79)
18.73(18.72)
13.57(13.57)
9.55(9.55)
6.51(6.50)
9.52(9.53)
6.70(6.68)
9.72(9.70)
6.25(6.25)
9.01(9.00)
6.13(6.10)
8.88(8.90)
14.31(14.30)
---
7.59(7.61)
---
(
H
19
F
3
N
6
O
3
Chaining yellow
Blessed red
(
) [VO (HTMeA)(H
2
O)](SO
4
)
48.93
--
14.26(14.25)
---
7.56(7.55)
---
(
673.49/673.51,VO (II)-5b)
)(C20 S)
478.45),5c-HTPA
) [VO (HTPA)(H O)](SO
659.47/658.32,VO (II)-5c)
)(C20 16ClF S)
512.89),5d-HTCA
) [VO (HTCA)](H O)
711.93,VO (II)-5d)
) (C20 S)
523.45),5e-HTNA
H
17 3
F N
6
O
3
Chaining yellow
Blessed red
(
2
4
)
49.67
--
14.57(14.80)
---
7.72(7.72)
---
(
H
3
N
6
O
3
Chaining yellow
Bluish green
Faint brown
Bluish green
(
2
2
.(SO
4
)
46.93
--
13.49(13.50)
---
7.16(7.15)
---
(
16 3 7 5
H F N O
(
0) [VO (SO
4
)(HTNA)]
5.86
13.30(13.30)
7.05(7.07)
(
H
2
O)
2
(722.48/721.47,VO
(
II)-5e)
1
13
TABLE 2
Compounds
H, C NMR data for triazole derivatives (5b, c & e)
1
13
H NMR
C NMR
5
b, (4-Me)
1.42 (t, J = 7.65 Hz, 3H, CH
J = 7.65 Hz, 2H, CH ), 6.88–6.90 (td, J = 7.65,
.85 Hz,1H, Ar-H), 6.98 (d, J = 7.65 Hz, 1H, Ar-H),
.15–7.16 (dd, J = 7.65, 1.7 Hz, 1H, Ar-H), 7.27–7.29 (td,
3
), 2.45 (s, 3H, CH
3
), 4.45 (q,
3 3 2
14.19 (CH ), 21.25 (CH ), 63.21 (CH ), 117.11, 117.20,
2
117.86, 119.15, 119.59, 123.55, 129.73, 130.48, 131.60,
135.96, 138.32, 143.32, 145.71, 157.52 (N=CH), 158.27
(C=O), 166.51 (=C-OH).
0
7
J = 7.65. 1.7 Hz, 2H, Ar-H), 7.32 (d, J = 7.65 Hz, 2H, Ar-
H), 7.67 (d, J = 8.5 Hz, 2H, Ar-H), 7.77 (s, 1H, N=CH),
8
.73(s, 1H, OH), 10.03 (s, 1H, NH).
1.41 (t, J = 6.8 Hz, 3H, CH ), 4.45 (q, J = 6.8 Hz, 2H,
CH ), 6.88–6.90 (td, J = 7.65,0.85 Hz,1H, Ar-H), 6.98 (d,
J = 7.65 Hz, 1H, Ar-H), 7.14–7.15 (dd, J = 7.65, 1.7 Hz,
H, Ar-H), 7.25–7.55 (m, 4H, Ar-H), 7.76 (s, 1H,
N=CH), 7.82 (d, J = 8.5 Hz, 2H, Ar-H), 8.65 (s, 1H, OH),
0.02 (s, 1H, NH).
1.44 (t, J = 6.8 Hz, 3H, CH
CH ), 6.92 (t, J = 6.8 Hz,1H, Ar-H), 6.99 (d, J = 7.65 Hz,
5
c, (H)
3
3 2
14.18 (CH ), 63.24 (CH ), 117.11, 118.16, 119.61, 123.55,
2
127.75, 128.09, 129.17, 130.49, 130.70, 131.62, 138.51,
143.51, 145.75, 157.51 (N=CH), 158.26 (C=O),
166.31(=C-OH).
1
1
5
e, (4-NO
2
)
3
), 4.48 (q, J = 7.65 Hz, 2H,
3 2
12.15 (CH ), 63.63 (CH ), 116.93, 117.18, 117.72, 119.01,
2
119.79, 122.39, 124.76, 130.75, 131.99, 143.64, 145.38,
145.76, 146.57, 157.58 (N=CH), 157.82 (C=O), 165.57
(=C-OH).
1H, Ar-H), 7.21–7.22 (dd, J = 6.8, 0.85 Hz, 1H, Ar-H),
.30–7.31 (td, J = 7.65, 0.85 Hz, 1H, Ar-H), 7.86 (s, 1H,
7
N=CH), 8.22 (d, J = 9.35 Hz, 2H, Ar-H), 8.39 (d,
J = 9.35 Hz, 2H, Ar-H), 8.59 (s, 1H, OH), 9.94 (s, 1H,
NH).
and then added to ligand solution drop-wisely. Each reac-
tion mixture suffered reflux over 10 hr, followed by
5, for minimizing the medium acidity. The colored VO
(II)-triazole complexes were collected by filtration and
washed by methanol, diethyl ether and leaved for dryness
in vacuum desiccators under CaCl2.
adding 0.5 g sodium acetate (in 5 ml bi-distilled H O), for
2
precipitation. This addition conducted the pH value to ≈

4
of 16
EL-METWALY ET AL.
TABLE 3 Significant IR bands (cm− ) of triazole derivatives (5a-e) and their VO (II) complexes
1
ν
(C=O)
ν
ν
(C=N)s
&
ν
C-
δr &
δw(H
ν
M-
ν
M-
ν
M-
Compounds
ν
OH,
ν
NH
ester
(N=N)
δ
(NH)
S
ν
as(SO4)
ν
s(SO4)
2
O)
ν
V=O
O
N
S
1)(C21H
19 3
F N
6
O
4
S)
3427,3304
1724
1630,1577,
513
1445
616
---
---
---
---
---
---
---
1
2
) [VO (HTMoA)](SO
)(C21 S)
4
)
3432,3296
3429,3257
---
1632, 1550
1638, 1575,
---
587
622
Ionic at 1410
781, 613
---
977
550
---
441
---
415
---
3
H
19
F
3
N
6
O
3
1724
1452
---
---
---
1526
4
5
6
7
8
9
1
) [VO +(HTMeA)
O)](SO
)(C20
478.45)
) [VO (HTPA)(H
SO
)(C20
B.c. at 3424
3425,3301
---
1636, 1571
---
615
612
622
609
613
625
615
Ionic at 1412
840, 638
---
1120
---
539
---
440
---
417
---
(
H
2
4
)
H
17
F
3
N
6
O
3
S)
1723
---
1633,1578,
1534
1444
---
---
-- -
(
2
O)]
B.c. at 3435
3434, 3263
B.c. at 3433
3441, 3227
B.c. at 3430
1639, 1566
Ionic at 1414
761, 641
---
1139
---
536
---
446
---
419
---
(
4
)
H
16ClF
3
N
6
O
3
S)
1728
---
1642,
1452
---
---
---
1575,1539
) [VO (HTCA)](H
2
O)
2
.
1639, 1565
1597, 1510
1618, 1568
Ionic at 1411
779, 661
---
982
---
587
---
441
---
415
---
(
SO
4
)
) (C20H
F
16 3
N
7
O
5
S)
1696
---
1447
---
---
---
(
523.45)
0) [VO (SO
O)
4
)(HTNA)]
1411
1305
810, 757
949
536
445
418
(
H
2
2
B. c. Broad centered
3
.3 | Thermodynamic parameters
corresponding VO (II) complexes, were optimized by
RTD-B3LYP-FC method by different base sets. After
finishing the orientation process, essential files were
extracted (log & chk). All that files were visualized over
The kinetic and thermodynamic parameteres were esti-
mated over DTG curves for VO (II)-triazole complexes.
The order (n), activation energy (E) as well as; ΔH, ΔS
and ΔG, were the parameteres under consideration. The
elected stages, correspond to the degradation for heavy-
massed moiety inside the coordination sphere. Also, such
stages have strict boarders with defined fraction decom-
pose (α) at each temperature point inside the step.
[
25]
Gauss-View program
screen, to identify and estimate
characteristics. Such identification was conducted after
applying numbering scheme upon optimized structures.
Variable physical parameters were calculated based on
frontier energy gaps (ELUMO- EHOMO), through known
[
26,27]
equations
as well as others extracted from log files.
[15–22]
Varible researchersr
treated with such study and
developed equations for this purpose. Here we already
[
16]
[22]
selected Coat-Redfern
and Horowitz-Metzger
equa-
3.6 | Molecular operating
environmental-docking (MOE)
tions, among them, for calculating the parameters.
MOE is the recent docking module (MOE, Vs. 2015) used
to simulate the interference between tested compound and
3.4 | Analysis techniques
[28]
functional cell-proteins
This simulation process was
All equipments used for analyzing new synthesizes were
displayed in Scheme 1S. The vanadium content as well as
sulfur contents were evaluated using standard analytical
conducted onto all synthesizes (ligands & complexes)
against 3s7s and 5jm5 proteins. This study is a preliminary
examination, used to give a broad view about the extent of
effectiveness for the tested compound (inhibitor) against
selected pathogen. 3s7s is the crystal structure of human
placental aromatase with breast cancer drug. While, 5jm5
is the AKR1C3 based pro-drug TH3424, which has a
potent anti-tumor activity against liver cancer. Firstly,
each tested compound was treated towards energy mini-
mization process, to configure stabilized structures. This is
[23]
methods.
3.5 | Conformational study
The best structural forms were extracted by applying
[24]
Gaussian 09 program.
All triazole derivatives and their

EL-METWALY ET AL.
5 of 16
1
13
FIGURE 2
H & C NMR spectra of ethyl 2-((4-((2-hydroxybenzylidene)amino)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-yl)thio)-2-(2-(4-
methylphenyl)hydrazineylidene)acetate (5b)
followed by, addition of atomic charges and regulating the
potential energy as well as other parameters by MMFF94x
force field. That compound was saved in new database as
MDB file then be ready for docking study. Secondly and
after removing water molecules, each selected co-crystal-
line protein, was treated by adding hydrogen-atoms over
amino-acids receptors. Then, the potential energy was
fixed, the site finder was regulated and also domains over
length and scoring value of energy. The only effective H-
bonding mustn't exceed than 3.5 Å. The docking validation
patterns as well as surfaces & maps, were extracted after
ligand interaction process over line domains. To rank the
inhibition efficiency, the scoring energy, bond lengths as
well as receptors, must be considered.
[29]
alpha-site sphere.
So, the two sides are ready for simu-
4 | RESULTS AND DISCUSSION
4.1 | General characteristics
lation process, then the docking started till the process
accomplished. Each process was the average of 30 poses
by using London dG scoring function, which improved by
triangle Matcher methods over two times. With respect to
each process, essential interaction parameters were
extracted as; ligand type, interaction type, receptors, bond-
All synthesized VO (II) complexes were stable at room
ꢀ
temperature, having high melting points (300 C) and
non-hygroscopic. 1:1 was the molar ratio compatible with

6
of 16
EL-METWALY ET AL.
all complexes (Table 1) based on analytical investigations
elemental content & mass). Regarding the molar con-
appeared after tautomerism in combination with ester-
carbonyl. This proposal was advocated by the appearance
of υ (N=N) band, which attached with complete demise
of υ(C=O) and υ (NH) bands. Although, the demised
bands were appeared as clear as sun in free ligands spec-
(
−3
ductivity (Λ , for 10 M in DMSO) values, were fall
m
exactly in mono-anionic conducting feature, except
[30]
[
VO (SO )(HTNA)](H O) ] complex
. This feature
4
2
2
−
1
supported by the high ionic-image covering-sulfate
group, which suffered reduction in VO (II)-5e complex,
without a clear known cause for that. There was a clear
contrast in colors, which points to different structural
forms that signifies the role of p-substituent.
tra at ≈ 1724 and 3300 cm , respectively. iii) The appear-
−
1
ance of new bands at ≈ 1410 cm signifies the presence
of sulfate ion in all complexes except VO (II)-5e complex.
While and regarding VO (II)-5e complex, two new bands
−
1
were recorded at; 1411 and 1305 cm that point to
[
33]
mono-dentate sulfate group
This proposal was obvi-
ously discriminated by molar conductivity values
(as mentioned previously). iv) Water molecules were
interfered inside and/or outside the coordination sphere
that inferred by appearance of δr (H O) & δw(H O)
4
.2 | The coordination mode
It is worthy to note that, the aim of our study was firstly
focused on using multi-central ligands to raise the oppor-
tunity for poly nuclear complexes on behalf of stabilized
mono-nuclear chelates. The analytical results suggested
stabilized mono-nuclear-VO (II) chelates instead of poly-
nuclear as planned. The chelation-process was accom-
plished through poly-dentate mode of bonding from coor-
dinating-ligands (5a-e). A strange behavior was recorded
with coordinating triazoles 5a-e, they appeared clearly in
2
2
bands. v) New band emerged to υ(V=O) at; ≈ 970 and
−
1
1120 cm , elucidates the presence of vanadyl atom in
two various geometries, square-pyramidal and octahe-
[
34]
dral, respectively
vi) Finally the M-L bands were
assigned for υ(V-O), υ(V-N) and υ(V-S) in all complexes
except VO (II)-5e with respect to υ(V-S) band, which is
obscured.
[31]
enolate-ester tautomer,
which stabilized only through
All triazole derivatives displayed four-
dentate mode of bonding towards VO (II) atom through,
[32]
complexation.
4.3 | UV–vis spectral investigation
1
0
23
OH (phenol), C=N , S and N=N except, 5e derivative.
This exception of ethyl 2-((4-((2-hydroxybenzylidene)
amino)-5-(trifluoromethyl)-4H-1,2,4-triazol-3-yl)thio)-2-
This analysis was performed for all complexes in DMSO
solvent (Figures 3S), to suggest the appropriate geometry
around mono-nuclear atom (V=O). All influential transi-
tion-bands and magnetic moments were gathered and
displayed in Table 4. Charge transfer bands were
(
(
2-(4-nitrophenyl) hydrazineeylidene)acetate derivative
5e,tri-dentate), may refer to inductive effect of nitro
−
1
group. Such significantly orients to lack of electron-cloud
over N=N group via resonance contribution. The com-
parative view upon coupled spectra (ligand & complex),
reveal the following remarks onto influential functional
bands (Table 3); i) Regarding υ (OH), υ(C=N ), υ(C-S)
bands, suffered a noticeable lower or high-shift in all
complexes, which point to their coordination. ii) Other
additive contributing center was N=N group, which
appeared close to visible region (22,075–26,596 cm ),
due to intensive conjugation of chromophoric groups
inside ligands. Such will lead up to depth-colors that
[
35]
observed for free ligands and their complexes.
Func-
10
tional d-d transitions, obviously differentiate between the
five complexes and appeared matched strongly with their
colors. The spectra of VO (II)-5a (olive-green), VO (II)-5d
and VO (II)-5e(bluish green), displayed bands that signify
TABLE 4 Electronic transition bands (cm− ) for VO (II)- triazole complexes
1
μ (eff) (B.
M.)
Dq
(cm
d-d transition bands
charge transfer bands
(cm )
Proposed
geometry
−
1
−1
−1
Complexes
)
(cm
)
1
) [VO (HTMoA)](SO
) [VO (HTMeA)(H O)]
SO
) [VO (HTPA)(H
SO
) [VO (HTCA)](H
SO
) [VO (SO
O)
4
)
1.71
1.71
----
15,152
25,907; 22,124
26,316
Square-pyramidal
Octahedral
2
2
1388.9
1282.1
1117.3
1234.6
21,053; 17,241; 13,889
19,305; 18,857; 12,821
16, 651; 11,173
(
4
)
3
4
5
2
O)]
O)
1.73
1.74
1.72
25,907; 23,585
Octahedral
(
4
)
2
2
.
26,596; 25,381; 22,075
26,178; 23,041
Square-pyramidal
Square-pyramidal
(
4
)
4
)(HTNA)]
16,700;12,346
(
H
2
2

EL-METWALY ET AL.
7 of 16
1
square-pyramidal geometry with VO central atom. The
with d systems with negligible influence for M-M inter-
action. This magnetic feature is considered a further sup-
port for suggesting one central atom (V=O) inside
coordination sphere.
2
2
2
2
transitions of B ! E(υ ) and B ! B (υ ) that char-
2
1
2
1
2
acterize square-pyramidal arrangement (Figure 3), were
−1
recorded at; 11173–12346
&
15152–16,700 cm .
Whereas, VO (II)-5b and VO (II)-5c (blessed-red) com-
plexes, displayed bands point to distorted octahedral
geometry with VO central atom (Figure 3). The trans-
4.4 | ESR study
2
2
itions
of
B g(dxy)
!
Eg(υ )(dxz,dyz),
2
1
2
2
2
2
2
2
2
ꢀ
B g(dxy) ! B g(dx -y )(υ ) and B g(dxy) ! A g(dz )
EPR spectra were obtained at 25 C (DPPH standard &
2
1
2
2
1
(
υ ), which attribute to distorted octahedral arrange-
3
υ = 9.435 GHz) for three VO (II)-triazole(5a-c) complexes
(as example, Figures 4 & 4S). Eight hyperfine-splitting
lines (I = 7/2) were appeared fairly clear and correspond
[
33]
ment
were fully appeared. Such three transitions were
−
1
respectively recorded at; 13,889, 17,241 and 21,053 cm
in VO (II)-5b complex, while at; 12,821, 18,857 and
2
2
to D -spectral term with T g ground. In C or C4v sys-
2
2v
−
1
1
9,305 cm in VO (II)-5c complex. Crystal field stabiliza-
tems, three sets or two sets of lines were expected, respec-
tion energy values (Dq) were estimated from first transi-
tively and already noticed upon the spectra that favor the
2
2
[37]
tion ( B g ! B g (υ ) = 10Dq) for most complexes and
presence of one central atom (VO)
. All Hamiltonian
2
1
1
[36]
fall in the normal range.
The magnetic susceptibility
parameters as, molecular orbital, isotropic and aniso-
tropic for VO (II) complexes were calculated and
values (μeff from 1.71 to 1.74 BM) agreed comfortably
FIGURE 3 The optimized structures of VO(II)-traizole complexes

8
of 16
EL-METWALY ET AL.
displayed (Table 5). dxy is the ground orbital recorded
with three VO (II) complexes according to the following
and A ) were taken as negative values, to obtain consid-
⊥
2
2
erable positive β and α values. From electronic spectra
of VO (II) complexes, the υ (E ) and υ (E ,) values
[38]
Hamiltonian order, g// g⊥ ge.
Isotropic and aniso-
1
1
2
2
−1
tropic parameters were estimated from the following
expressions; A = (A +2A ) /3 and g = (g + 2 g )
(cm ), were used to calculate spin-orbital coupling con-
stant (λ) from the following relations; g =g –(8 λ/E )
o
//
⊥
o
//
⊥
//
e
1
[39]
⊥
/3.
Such parameters (A and g ) are highly deviated
and g = g –(2 λ/E ). The calculated values of λ, were
from 126.94–146.38 cm range, which suffer high reduc-
tion from that of free V ion (250 cm ). This minimiza-
tion, clarifies the role of substantial π-bonding in V=O
o
o
e
2
−
1
from that of free electron (g = 2.0023), which advocate
e
+
4
−1
distorted tetragonal geometry. Exchange- interaction
parameter (G) was calculated from this equation;
G = (g −2.0023)/(g - 2.0023). Its values appeared far from
+
2
[
33]
ion, although the values within the reasonable limit.
//
⊥
normal (G = 4), which indicate significant inter-
The dipolar-term (p) was calculated from the following
7
ðA== −A⊥
Þ
action inside the complex that relatively negligible on
equation:p = 6
by which and if the A as nega-
//
+ 3=2ðλ=ΔE1Þ
[
40]
hyperfine-splitting.
Molecular orbital parameters
tive and A⊥ as positive, the p value will exceed than
270 G and far from the normal range.
2
2
[42]
(
β
and α ) were estimated from the following
So that, the
[41]
equations;
values of A and A were taken as negative value.
//
⊥
McGarvey calculated the p value for vanadyl complexes
ꢀ
ꢁ
7
6
2
A==
A⊥
5
14
9
14
to be +136G, the calculated values not deviate much
β2 =
−
+
+ g − g⊥ − ge &a2
=
=
[42]
p
p
from that previously mentioned.
Also, Fermi-contact
:0023−Δg
term (K), which considered the indicator of outer-shell
electron with atomic nucleus, were estimated from this
expression; K = −(A /p)-(g -g ) and fall in normal
=
2
8
λβ
o
e
o
[
43]
known.
The reduction of A value versus g value, is
// //
2
2
β and α values were close to unity, which indicate the
high ionic characteristic of in-plane σ- and π- bonding
known by a tetrahedral distortion indicator (f = g /
//
[
40]
A )
the calculated values clarify the high distortion of
/
/
[40]
around vanadyl.
Hyperfine-coupling constants (A//
all complexes.
FIGURE 4 EPR spectrum of
VO(II)-5b complex
TABLE 5 ESR spectral parameters for some VO (II)- triazole complexes (A and p x10−4
)
λ (cm−
144.51
126.94
146.38
1
)
A
A
G
p
k
α
2
β
2
Complex
g
//
g
⊥
g
o
A
11
f
⊥
o
1) [VO (HTMoA)](SO
2) [VO (HTMeA)(H O)](SO
3) [VO (HTPA)(H O)](SO
4
)
1.9260
1.9434
1.9402
1.9638
1.9539
1.9596
1.9512
1.9504
1.9531
175.79
180.41
185.19
109.56
107.72
104.77
71.98
76.91
73.32
106.58
111.41
110.61
1.9818
1.2169
1.4543
120.82
120.53
130.20
0.933
0.976
0.868
0.7206
0.8867
0.9752
0.9294
0.9086
0.8124
2
4
)
2
4
)

EL-METWALY ET AL.
9 of 16
4
.5 | Mass spectral-analysis
which signify the thermal stability inside the coordina-
tion sphere. This feature represents the great influence of
metal atom on thermal-stability of organic compounds.
Mass spectral analysis was carried out at 70 ev, under
heating rate of 40 C/min and covered upon broad range
ꢀ
The residual part was mainly recorded upon reaching
ꢀ
of mass (50–1000)(Figures 5 & 5S). This analytical tool
used to emphasis on the molecular formula for new syn-
thesizes, especially with fail in executing x-ray single
crystal. VO (II)-5b, VO (II)-5c and VO (II)-5e, were the
elected-complexes spectrally-scanned for this analysis, to
confirm their formulae. The mass spectrum of VO (II)-5b
complex (Figure 5), displayed matched molecular ion
steady stage up to 780 C, and coincides with VO , VO or
2
VO + 2C, in mono-nuclear complexes. The relative har-
mony between calculated mass-loss with the found
values in most stages, reflects the definite assignment for
stage-boarder. Moreover, kinetics and thermodynamic
parameters were estimated over heavily-massed stage in
rd
th
each DTG/DTA curves (3 &4 ). This selection aims to
investigate the degree of stability inside the coordination
sphere as well as the kinetic behavior of decomposition-
reaction. E, ΔH, ΔS and ΔG were the thermodynamic
parameters calculated from, ΔH = E + PV, ΔG = ΔH-
+
peak (m/z = 673.51, I = 15%) with M that already pro-
posed (calcd. 673.49). The fragmentation pattern dis-
played the base peak at m/z = 347.31(I = 100%) which
coincide the massive moiety attached with central atom
*
(see the figure). Moreover, the metal isotopes were appar-
TΔS and ΔS = R ln (Ah/K T ) equations. Whereas; k
b
S
B
[44]
ently recorded at m/z = 51.58 . Also, the other two-
spectra (Figure 5S) exhibited molecular ion peaks (m/
z = 658.32 and 721.47) attributing to M -1. Also, the suc-
cessful fragmentation displayed clear patterns with
intense peaks which include peaks attributing to metal
isotopes also (m/z = 50.64 and 53.47).
and h are Boltzmann and Plank's constants, respectively,
while T is the midpoint temperature of the stage. Frac-
s
+
tion decompose values (α) at definite temperatures (t),
[
17]
were implemented in Coats–Redfern
and Horowitz–
[
22]
Metzger equations (Figure 7S), to calculate aimed
parameters under constant heating rate (Table 1S). The
two referenced methods were applied to confirm each
other's. The data lead to the following remarks; i) high
activation energy (E) values, which indicate high stability
of such stage. ii) The values of ΔS represent in its sign
(−ve), pointed to high randomness-degree in non-
spontaneous reaction. iii) The values of ΔH represent in
its sign (+ve), pointed to endothermic-characteristic of
decomposition stage. iv) The values of ΔG were appeared
raised, as logical values in-agreement with ΔH(+ve) and
ΔS(−ve) values.
4.6 | TGA analysis
TGA/DTG curves (Figure 6S) for complexes, were
extracted at constant heating rate (10 C min ) and
under nitrogenous environment onto 20-900 C, tempera-
ture range. Thermal degradation hypotheses were
exhibited in Table 6, to prove the formulae suggested and
distinction for associating water molecules. All complexes
displayed complete distortion over four to five degrada-
ꢀ
−1
ꢀ
ꢀ
tion stages reached to ≈ 780 C. The high thermal stabil-
ity was recorded with VO (II)-5a-c complexes only, but
the others appeared with reduced thermal stability. This
4.7 | XRD analysis
ꢀ
ꢀ
reduction is referring to crystal water molecules attached
XRD patterns were obtained at10 < 2θ <80 rang for
three complexes (Figures 6 & 8S) as instance, to examine
their lattice-dynamic and purity. Many dedicated
ꢀ
(
2H O). The expel of ionic-sulfate (up to ≈ 240 C) differs
2
ꢀ
by acceptable-extent (up to 365 C) than that covalently-
bonded with VO (II)-5e complex. The bulky-mass
decomposed was recorded with third or fourth stage,
[
45]
methods
are being available to investigate layer-thick-
ness and chemical composition. The diffused x-ray used
FIGURE 5 Mass spectrum of
VO(II)-5b complex

10 of 16
EL-METWALY ET AL.
TABLE 6 TGA pathway proposed for VO (II)- triazole complexes
Weight loss; Calcd (Found
%)
ꢀ
Compounds
Steps
Temp. range( C)
Decomposed
st
1
2
3
4
) [VO
1
2
125.85–278.90 292.62–410.66
415.52–582.20 584.47–776.9
-SO
C
4
-C
7
H
7
O -C
4
H
6
N
2
O
2
S -
14.31(14.33) 15.94(15.94)
21.75(21.81) 35.60(35.57)
12.35(12.35)
ed rd th
(
(
HTMoA)]
SO
3
4
10
H
6
F
3
N
4
VO
2
4
)
residue
st
) [VO
1
2
105.11–205.71 253.33–352.30
424.12–575.15 651.71–753.90
-H
C
2
O + SO
N -C
4
-C
7
H
H
6
NO -
OS VO
2
16.94(16.94) 17.82(17.80)
33.56(33.60) 19.30(19.31)
12.32(12.35)
ed rd th
(
(
HTMeA)
O)](SO
3
4
10
H
7
F
3
4
6
N
2
H
2
4
)
residue
st
) [VO (HTPA)
O)](SO
1
2
110.21–212.90 251.56–335.09
410.73–550.17 572.94–764.05
-H
2
O + SO
S + C
VO + 2C
-2H O -SO
S -C
4
-C
6
H
5
-C
7
H
6
NO -
17.30(17.33) 11.68(11.66)
18.20(18.19) 39.12(39.04)
13.79(13.78)
ed rd th
(
H
2
4
)
3
4
C
3
F
3
N
3
2
H
7
N
2
O
2
residue
st
) [VO
1
2
34.73–85.42 151.20–291.17
300.50–450.61 450.37–578.92
634.87–755.73
2
4
-C10
H
6
F
3
N
4
-
5.06(5.06) 13.49(13.51)
33.59(33.55) 16.45(16.40)
19.74(19.77) 11.65(11.71)
ed rd th
(
(
HTCA)]
O) .(SO
3
th
4
C
4
H
5
O
2
6 5 2 2
H ClN VO
H
2
2
4
)
5
residue
st
5
) [VO (SO
4
)
1
2
43.26–121.85 198.81–365.05
365.05–602.11 603.71–748.92
-2H
C
2
O -C
4
H
6
N
2
O
2
+ SO
4
-
4.99(5.02) 29.08(29.09)
39.73(39.77) 16.89(16.84)
9.27(9.28)
ed rd th
(
(
HTNA)]
O)
3
4
13
H
6
F
3
N
4
OS -C NO VO
6
H
4
2
th
H
2
2
5
residue
to determine cross-correlations and distortion, while the
scattered used to determine size, shape and orientation of
particles in solid component. The patterns of VO (II)-5b
and VO (II)-5c complexes, reflect their nano-crystalline
nature in well-building crystal, while VO (II)-5a appeared
relatively amorphous. The crystallite-particulate parame-
ters, were calculated and displayed (Table 7) using
FWHM method. The particulate sizes, 2θ, d spacing,
FWHM, relative intensity, crystal strain (ε) and
dislocation density (δ) were such parameters calculated
[
46]
using standard equations.
The sizes calculated
(4.8657 & 1.0200 Å) fall in nanometer range and the d-
spacing values were apparently matched (≈ 2.79 Å). The
minimized crystal strain (ε) and dislocation-density (δ,
−2
Å ) of VO (II)-5b complex, point to regular-crystal lat-
tice. While, that values of VO (II)-5c complex appeared
high, which reflect a significant distortion in crystal lat-
tice around dislocation lines.
FIGURE 6 XRD pattern of VO(II)-5b complex

EL-METWALY ET AL.
11 of 16
4
.8 | Conformational study
orbital appeared in the opposite side for HOMO as a
logical and expected feature. While, such orbital
appeared focused around central-atom in all VO (II)-
complexes.
All new synthesizes were suffered configuration till
optimization by using Gaussian09 program (Figures 3 &
9
S). The most fitted method adaptable for executing
the modeling, was RTD-B3LYP-FC under two distinct
base sets (3-21G & 6-31G). Essential computational
files were extracted (log & chk) and visualized over
Gauss-view screen, to extract important physical fea-
tures. Among that, the frontier energy gaps
4.9 | Estimated physical parameters
Χ, μ, η, s, ω and б were the parameter-symbols of;
electronegativity, chemical potential, global-hardness,
global-softness, global-electrophilicity and absolute-soft-
ness, respectively. Such parameters were calculated by
(
ΔE = ELUMO- EHOMO), which used to calculate signifi-
cant physical parameters (Table 2S). The HOMO &
LUMO figures exerted from chk files (Figures 10S&11S),
to clarify the impact of p-substituents on overall elec-
tron distribution upon molecular orbitals. Concerning
HOMO-images, such orbital was focused onto p-
substituted phenyl diazene moiety. This appearance
conducts to intensive- electronic feedback over triazole
ring. While, such orbital is fairly changed in VO (II)-
triazole complexes and appeared extended to surround-
ing of central-atom. Concerning to LUMO-images, such
[26,27]
using known-equations and exhibited (Table 2S)
Concerning such parameters and from comparative
point of view, we concluded the following important
notices; i) reduced energy-gaps, were recorded with all
VO (II) complexes, in comparing to free-traizoles. This
points to influential effect of central atom on raising
the complex reactivity with facilitated electronic transi-
tion. ii) Electrophilicity parameter (ω) is considered
the measure of compound-reactivity through its ability
TABLE 7 XRD parameters using FWHM for nano-crystalline complexes
δ(Å−
2
)
FWHM
0.3030
Compounds
Size (Å)
4.8657
2θ
Intensity
48.70
d-spacing (Å)
2.79151
ε
1
2
) VO (II)-5b
)VO (II)-5c
32.037
31.945
0.09202
3.31502
0.04224
0.96117
1.0200
25.40
2.79932
0.6222
FIGURE 7 Electrostatic maps for selected traizole derivatives and their VO(II) complexes

12 of 16
EL-METWALY ET AL.
for electron-acquiring from surrounding. The general
enhancement in VO (II) complexes, was considered
reactivity progression than the original triazoles
themselves. The high value (0.680826 ev) was recorded
with VO (II)-5e complex, in coinciding with high
inductive effect of nitro-group p-substituent. iii)
FIGURE 8 Docking validation for VO(II) complexes against breast cancer protein (3s7s)

EL-METWALY ET AL.
13 of 16
Electronegativity (x) and chemical potential (μ) indexes
were the two opposing faces which point to the degree
of polarity upon the molecule, appeared high with 5e
and its complex. iv) Global- hardness (η) and softness
values indicate excellent biological behavior, which
[
49]
strongly expected from all VO (II) complexes
Other
significant outputs were extracted from log files and
also displayed (Table 3S). The formation energy (E, a.
u.), excitation energy (E, nm), oscillator strength (f)
and dipole moment (D, Debye) were the outputs of log
files. The reduced formation energy values recorded
with VO (II) complexes, discussed undoubted impact
(
S), also two opposing faces that indicate the degree of
flexibility of structure. This flexibility is favorable in
biological effectiveness, and also represents the priority
of complexes.[47a, 48] v) The absolute softness (б)
FIGURE 9 Surface-mapping of VO(II) complexes against breast cancer protein (3s7s)

14 of 16
EL-METWALY ET AL.
of metal atom in stability. Also, minimized oscillator
strength values beside the elevated excitation energy
values, reveal stability of electronic configuration
towards excitation. Moreover, dipole moment values
suffer noticeable elevation, which considerably
conclude the following remarks; i) scoring energy
values (Kcal/mol) were appeared excellent with all VO
(II) complexes beside 5c(−8.2548) 5e(−9.484) derivatives
against 3s7s protein only. While, the other negligible
untrue values were recorded with; 5b against 3s7s
(−9.0166) and 5d against 3s7s (−8.5299) & 5jm5
[50,51]
expected after coordination process
(−7.7136) proteins. This ignoring due to H-bonding
lengths, which exceed than the normal recognized
(3.5 Å). ii) The effective contributing sites with respect
to triazoles were, S19 and O18, 35, 36, while that with
respect to complexes were, N10, 23, 24; S20; O18,19,59
and F9.iii) The effective helix-receptors versus triazoles
were, Arginine, Methionine, Cysteine and Lysine.
Meanwhile and with respect to VO (II) complexes, were
Glutamate, Glutamine, Aspartate and Lysine. iv) The
interacting types in triazoles-protein complexes were,
H- acceptor and H-donor, while that for VO
(II) complexes, were ionic, pi-H, H-donor and H-accep-
4
.10 | Molecular electrostatic potential
(MEP)
Electrostatic maps (Figures 7 & 12S) were built after
distributing charges over surfaces and contours then
demonstrating new cube over surfaces. The electron-
density over triazole derivatives, was appeared from
.806 x10− to 8.889 x10
appeared from 0.1120 to 6.289x10
II) complexes. As we see, the magnitude of electron
2
−2
range. Meanwhile, was
7
−
2
range in VO
(
[
29]
density was elevated after complexation in coinciding
with the state of dipole moments. Generally, this maps
help in discovering electron-rich centers, which have a
tor
. v) Generally, the energy content values (−8.7 to
−1.2 Kcal/mol) signify the high stability of docking
complexes. This mentioned data point to promising
broad-spectrum of all VO (II) complexes as well as 5c
and 5e, against breast-cancer. Whereas, all outputs
according to liver cancer protein, point to mild-inhibi-
tion activity. Moreover, the interaction validity patterns
(Figures 8 & 13S) as well as surface-maps (Figures 9 &
14S) of all docking complexes, were extracted to con-
firm interaction features. According to interaction pat-
terns with 5jm5 protein, we notice that, an extended
ligand-exposure beside shortage in receptors were
appeared. While, polar side-chain acceptor and all back-
bone donors (basic, acidic and greasy) were also
recorded. According to interaction-patterns with 3s7s
protein, appeared with extended receptor-exposure
beside shortage in ligand-exposure especially with free
derivatives. While, the other interaction features (accep-
tor and donor types) were fully compatible. Finally, the
surface-mapping images (Figures 9 & 14S), which dem-
onstrated upon line-dommais, were strongly coincided
with interaction patterns. Strong interacting complexes
appeared almost hidden, while the others showed slight
surface-overlap. This study offers an good simulation
about what happened inside the infected cell during the
treatment with new compounds, before experimental
screening. Finally, promising feature may be expected
with all VO (II) complexes against breast-can (3s7s).
[29]
good opportunity for coordination.
The red and blue
colors are two discriminating-zones, point to electron-
rich (nucleophilic) and electron-poor centers (electro-
philic), respectively. While, the green color refers to
intermediate characteristic. It is worthy to note that,
the centers contributing in coordination as; N=N , C-
S and OH appeared with nucleophilic opportunity.
23
23
Concerning 5e derivative, the appearance of N=N
group as electrophilic-center, confirmed the suggestion
of its exclusion from coordination, which already
mentioned.
4.11 | Molecular operating environment
docking study
MOE simulation procedure, is the most recent compu-
tational study, which caused a great revolution in drug
industry. This tool deals with the interaction between
proposed drug (compound) and responsible protein of
definite infected-cell. Here, we examined the docking
for all triazole derivatives and their VO (II) complexes,
against two tumor cell proteins, 3s7s (breast-cancer)
and 5jm5 (liver-cancer). Each treatment consumed dif-
ferent time from another to finish. The data exported,
were the average of 30 trials through applying London
dG scoring function (Table 4S). Also, the docking vali-
dation (Figures 6 & 13S) as well as surface-mapping
5 | CONCLUSION
(Figures 7 & 14S), were extracting to recognize interac-
tion-features. Ligand kinds, receptors, interaction types,
H-bond lengths and scoring-energies were the interac-
tion-data extracted. From comparative point of view, we
Five new triazole derivatives were characterized and
then complexes with VO (II) ion. The new complexes
were completely described from analytical, spectral and

EL-METWALY ET AL.
15 of 16
conformational studies. Octahedral and square-pyrami-
dal were the structural forms proposed. Essential spec-
tral parameters were extracted from NMR, UV–Vis and
ESR spectra. Conformational study were implemented
to optimize new structural forms. MOE-docking mod-
ule, was implemented over all compounds towards
responsible infected cell-proteins. A promising inhibi-
tion activity was strongly expected with the complexes
against breast cancer protein (3s7s) in addition to 5c
and 5e derivatives.
[16] E. S. Freeman, B. Carroll, J. Phys.Chem. 1958, 62, 394.
[
[
[
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ACKNOWLEDGMENTS
V.
Barone,
B.
Mennucci,
G.
A.
Petersson,
Prof. Nashwa El-Metwaly and co-authors would like to
thank Deanship of Scientific Research at Umm Al-
Qura University (project ID: 17-SCI-1-03-0001) for the
financial support to this research extracted from the
project.
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ORCID
Nashwa El-Metwaly https://orcid.org/0000-0002-0619-
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How to cite this article: El-Metwaly N,
Farghaly TA, Elghalban MG. Synthesis, analytical
and spectral characterization for new VO (II)-
triazole complexes; conformational study beside
MOE docking simulation features. Appl
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Organometal Chem. 2020;e5505. https://doi.org/10.
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