New Vanadium Complexes with Aroylhydrazone Ligands: Synthesis, Structures, and Biochemical Properties

Article abstract of DOI:10.1080/15533174.2013.819898

The aroylhydrazone Schiff base ligands [N′-(2-hydroxynaphthyl)ethylidene]-4-nitrobenzohydrazide (H₂L^a) and N′-(3,5-dichloro-2-hydroxybenzylidene)-3-nitrobenzohydrazide (H₂L^b) reacting with VO(acac)₂ in methanol gave the complexes [VOL^a(OMe)]·0.5MeOH·0.6H₂O (1) and [VOL^b(OMe)(MeOH)] (2). Both complexes were characterized by elemental analyses and IR spectroscopic method in the solid state. Single crystal X-ray analysis was performed, which indicates that both complexes are mononuclear. The V atom in (1) is in a square pyramidal geometry, and that in (2) is in an octahedral geometry. V^IV in VO(acac)₂ was oxidized to V^V in the complexes by aerial oxygen during the synthesis and crystallization. Antibacterial activities of the aroylhydrazone ligands and the complexes have been studied on the strains Bacillus subtilis, Escherichia coli, and Staphylococcus aureus.

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New Vanadium Complexes with Aroylhydrazone
Ligands: Synthesis, Structures, and Biochemical
Properties
Ji-Lai Liua, Ming-Hui Sunb & Jing-Jun Mac
a Hebei Changshan Biochemical Pharmaceutical Co., Ltd., Shijiazhuang, P. R. China
b Department of Economics and Management, Hebei North University, Zhangjiakou, P. R.
China
c College of Sciences, Agricultural University of Hebei, Baoding, P. R. China
Accepted author version posted online: 14 Apr 2014.Published online: 02 Sep 2014.
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To cite this article: Ji-Lai Liu, Ming-Hui Sun & Jing-Jun Ma (2015) New Vanadium Complexes with Aroylhydrazone Ligands:
Synthesis, Structures, and Biochemical Properties, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal
Chemistry, 45:1, 117-121, DOI: 10.1080/15533174.2013.819898
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry (2015) 45, 117–121
Copyright © Taylor & Francis Group, LLC
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2013.819898
New Vanadium Complexes with Aroylhydrazone Ligands:
Synthesis, Structures, and Biochemical Properties
JI-LAI LIU1, MING-HUI SUN2, and JING-JUN MA3
1Hebei Changshan Biochemical Pharmaceutical Co., Ltd., Shijiazhuang, P. R. China
2Department of Economics and Management, Hebei North University, Zhangjiakou, P. R. China
3College of Sciences, Agricultural University of Hebei, Baoding, P. R. China
Received 25 April 2013; accepted 11 June 2013
The aroylhydrazone Schiff base ligands [N0-(2-hydroxynaphthyl)ethylidene]-4-nitrobenzohydrazide (H2La) and N0-(3,5-dichloro-2-
hydroxybenzylidene)-3-nitrobenzohydrazide (H2Lb) reacting with VO(acac)2 in methanol gave the complexes [VOLa(OMe)]¢
0.5MeOH¢0.6H2O (1) and [VOLb(OMe)(MeOH)] (2). Both complexes were characterized by elemental analyses and IR spectroscopic
method in the solid state. Single crystal X-ray analysis was performed, which indicates that both complexes are mononuclear. The V
atom in (1) is in a square pyramidal geometry, and that in (2) is in an octahedral geometry. VIV in VO(acac)2 was oxidized to VV in the
complexes by aerial oxygen during the synthesis and crystallization. Antibacterial activities of the aroylhydrazone ligands and the
complexes have been studied on the strains Bacillus subtilis, Escherichia coli, and Staphylococcus aureus.
Keywords: aroylhydrazone, biochemical property, crystal structure, vanadium complex
Introduction
and vanadium(IV) oxide acetylacetonate ([VO(acac)2]) were
purchased from Merck and Fluka, and used as received. The
The presence of vanadium(IV) and vanadium(V) compounds aroylhydrazone Schiff base ligands [N0-(2-hydroxynaphthyl)
in many vanadium-dependent enzymes, for instance, nitroge- ethylidene]-4-nitrobenzohydrazide (H2La) and N0-(3,5-
nases and haloperoxidases,[1–3] as well as insulin mimicking,[4,5] dichloro-2-hydroxybenzylidene)-3-nitrobenzohydrazide (H2Lb)
has stimulated the search for structural and functional models were prepared in over 90% yields by condensation reactions of
based on vanadium complexes. Moreover, oxovanadium com- 1-(2-hydroxynaphthalen-2-yl)ethanone with 4-nitrobenzohy-
plexes have been attracted tremendous attention for their ver- drazide, and 3,5-dichlorosalicylaldehyde with 3-nitrobenzohy-
satile catalytic properties in organic synthesis.[6–8] In recent drazide, respectively, in methanolic media, according to the
years, the remarkable biological activity of aroylhydrazones literature method.[16,17] All other chemicals and solvents used in
and the dependence of their mode of chelation with transition this work were of analytical grade available commercially and
metal ions in living systems have been of significant interest.[9–12] used without further purification. Elemental analyses (carbon,
Vanadium complexes of aroylhydrazones have also been hydrogen, and nitrogen) of the compounds were obtained from
reported to possess various antimicrobial activities.[13–15] Aim- a Carlo ERBA Model EA 1108 analyzer. Infrared spectra were
ing at obtaining new vanadium complexes with biological collected by using KBr pellets on a Jasco-5300 FT-IR spectro-
properties, in this article, two new vanadium complexes, [VOL- photometer (Leici Instrument Co., Shanghai, China). Solution
a(OMe)]¢0.5MeOH¢0.6H2O (1) and [VOLb(OMe)(MeOH)] (2), electrical conductivity was measured with a DDS-11A conduc-
were synthesized, characterized, and studied their activities tivity meter.
against Bacillus subtilis (B. subtilis), Escherichia coli (E. coli),
and Staphylococcus aureus (S. aureus).
Synthesis of [VOLa(OMe)]¢0.5MeOH¢0.6H2O (1)
Experimental
[VO(acac)2] (0.01 mmol, 2.65 g) dissolved in methanol
(30 mL) was added dropwise to a stirred methanolic solution
(30 mL) of H2La (0.01 mol, 3.49 g). The mixture was gently
refluxed for 2 h, then the most of the solvent was evaporated
by distillation. After cooling, the resulting brown solid was
filtered off, washed with cold methanol, and dried in a vac-
uum containing anhydrous CaCl2. Yield: 2.13 g (47%). Anal.
Calcd. for C41H38N6O14V2 (%): C, 52.35; H, 4.07; N, 8.93.
Found: C, 52.16; H, 3.95; N, 9.02. IR data (cm–1, KBr): 3386
(br), 1602 (s), 1563 (m), 1527 (m), 1481 (m), 1332 (w), 1287
Materials and Methods
1-(2-Hydroxynaphthalen-2-yl)ethanone, 3,5-dichlorosalicy-
laldehyde, 4-nitrobenzohydrazide, 3-nitrobenzohydrazide,
Address correspondence to Jing-Jun Ma, College of Sciences,
Agricultural University of Hebei, Baoding 071001, P. R. China.
E-mail: majingjun71@yahoo.cn

118
Liu et al.
Table 2. MIC values (mg mL¡1) of the tested compounds.
(m), 1255 (s), 1217 (m), 972 (s), 755 (m), 454 (w). Brown
block-like single crystals of the complex, suitable for single
crystal X-ray diffraction, were obtained by slow evaporation
of a methanol solution containing the complex.
B. subtilis
E. coli
S. aureus
H2La
>100
12.5
12.5
1.56
0.78
0.39
25
6.25
12.5
6.25
100
>100
25
12.5
3.13
3.13
1.56
H2Lb
(1)
(2)
Synthesis of [VOLb(OMe)(MeOH)] (2)
Penicillin
Kanamycin
Complex (2) was prepared by an analogous method to that
for complex (1), except for the replacement of H2La by H2Lb
(0.01 mol, 3.53 g). Yield: 2.72 g (56%). Anal. Calcd. for
C16H14Cl2N3O7V (%): C, 39.86; H, 2.93; N, 8.72. Found: C,
39.97; H, 3.05; N, 8.60. IR data (cm–1, KBr): 3351 (w), 1611
(s), 1555 (m), 1519 (m), 1473 (m), 1341 (m), 1293 (m), 1252
(s), 976 (s), 877 (w), 751 (m), 672 (w), 471 (w).
6.25
Antibacterial Assay
The antibacterial activities were tested against B. subtilis, E.
coli, and S. aureus using Mueller-Hinton medium. The MICs
(minimum inhibitory concentrations) of the test compounds
were determined by a colorimetric method using the dye MTT
[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bro-
mide].[19] A stock solution of the synthesized compound
(50 mg mL¡1) in dimethyl sulfoxide (DMSO) was prepared
and quantities of the test compounds were incorporated in a
specified quantity of sterilized liquid Mueller-Hinton medium.
A specified quantity of the medium containing the compound
was poured into microtitration plates. A suspension of the
microorganism was prepared to contain approximately 105 cfu
mL¡1 and applied to microtitration plates with serially diluted
compounds in DMSO to be tested and incubated at 37ꢀC for
24 h. After the MICs were visually determined on each of the
microtitration plates, 50 mL of PBS (phosphate buffered saline
0.01 mol L¡1, pH 7.4: Na2HPO4¢12H2O 2.9 g, KH2PO4
0.2 g, NaCl 8.0 g, KCl 0.2 g, distilled water 1000 mL) con-
taining 2 mg of MTT/mL was added to each well. Incubation
was continued at room temperature for 4–5 h. The content of
each well was removed and 100 mL of isopropanol containing
5% 1 mol L¡1 HCl was added to extract the dye. After 12 h of
incubation at room temperature, the optical density (OD) was
measured with a microplate reader at 550 nm. The antibiotics
kanamycin and penicillin were used as standard drugs. The
observed MIC values are given in Table 2.
X-Ray Crystallography
Suitable X-ray quality crystals of the complexes (1) and (2)
were pick up under a microscope and investigated in a dif-
fraction experiment at 298(2) K on a Bruker Apex II diffrac-
tꢀometer with monochromated Mo Ka radiation (λ D 0.71073
A) obtained from a graded multilayer X-ray optics. The
structures were solved by direct methods with SHELXS-
97,[18] and refined with full-matrix least-square techniques on
F2 with SHELXL-97.[18] The C- and O-bonded hydrogen
atoms were calculated in an idealized geometry, riding on
ꢀ
their parent atoms, ꢀwith distances restrained to 0.93–0.96 A
for C–H and 0.82 A for O–H. The crystal data and refine-
ment parameters are listed in Table 1.
Table 1. Crystallographic data for the complexes.
(1)
(2)
Chemical formula
Formula weight
Crystal system
C41H38N6O14V2
938.64
C16H14Cl2N3O7V
482.14
Triclinic
P-1
Monoclinic
P21/c
Space group
Unꢀit cell dimensions
a (A)
7.492(2)
14.131(3)
21.771(2)
75.572(2)
89.807(2)
79.842(1)
2195.2(8)
2
12.973(11)
18.279(15)
7.986(7)
90
90.03(6)
90
1894(3)
4
1.691
ꢀ
b (A)
Results and Discussion
ꢀ
c (A)
a (ꢀ)
b (ꢀ)
Synthesis and Characterization
g (ꢀ)
Reaction of VO(acac)2 with tridentate aroylhydrazone
ligands H2La and H2Lb in methanol, respectively, under aero-
bic conditions afforded neutral oxovanadium(V) complexes
(1) and (2). Most likely during the synthesis and crystalliza-
tion of the complexes from oxovanadium(IV) starting mate-
rial, the aerial oxygen acts as the oxidizing agent. Elemental
analyses of the complexes are consistent with the general
molecular formulae proposed by single crystal X-ray determi-
nation. In absolute methanolic solution, they are electrically
non-conducting.
ꢀ
V (A3)
Z
r (g cm¡3
)
)
1.420
0.498
m (mm¡1
0.852
Tmin, Tmax
0.9157, 0.9246
14,768
0.7841, 0.8025
14,885
4065
Reflections collected
Reflections unique
Reflections observed
[I > 2s(I)]
Parameters
Restraints
7820
4339
3006
610
30
268
1
R1, wR2 [I > 2s(I)]
R1, wR2 (all data)
Goodness of fit on F2
0.0960, 0.2387
0.1594, 0.3006
1.012
0.0874, 0.2094
0.1082, 0.2191
1.099
IR Spectroscopic Characteristics
Infrared spectra of the free aroylhydrazone ligands and their
complexes gave information about the coordination. The free

New Vanadium Complexes with Aroylhydrazone Ligands
119
Fig. 1. Structure of the V1 molecule of complex (1) with the atom labeling scheme. All non-hydrogen atoms are represented at 30%
probability thermal ellipsoids.
ligands display broad bands in the region 3350–3450 cm¡1 Description of the Crystal Structure of (2)
and weak and sharp bands at about 3270 cm¡1. These bands
Molecular structure and the atom numbering scheme for com-
are possibly due to the OꢁꢁH and NꢁꢁH stretches. However,
plex (2) is depicted in Figure 2. Selected bond lengths and
the sharp bands are absent in the spectra of the complexes.
The absence of the n(CHO) bands, present in the free aroyl-
ꢀ
hydrazone ligands H2La and H2Lb at 1660 and 1651 cm¡1
,
Table 3. Selected bond lengths (A) and angles (ꢀ) for the
respectively, indicates the enolization of the amide function- complexes.
ality upon coordination to the V atom. Strong bands
observed at 1602 cm¡1 for (1) and 1611 cm¡1 for (2) can be
(1)
Bond lengths (A)
1.908(5)
ꢀ
attributed to the stretching vibrations of the azomethine
V1–O3
V1–O4
V1–O6
V2–O9
V2–O11
V2–N6
1.830(5)
1.821(5)
1.908(5)
1.809(5)
2.107(6)
groups, nC=N.
[20] The spectra of the complexes display typical
V1–O5
V1–N3
V2–O10
V2–O12
1.578(5)
2.110(6)
1.829(5)
1.582(5)
and intense bands at 972 cm¡1 for (1) and 976 cm¡1 for (2),
which are assigned to the stretches of the VHO bonds.[21]
Bond angles (ꢀ)
O5–V1–O6
O6–V1–O4
O6–V1–O3
O5–V1–N3
O4–V1–N3
O12–V2–O11
O11–V2–O10
O11–V2–O9
O12–V2–N6
O10–V2–N6
103.7(3)
104.9(2)
89.7(2)
98.2(2)
81.9(2)
103.9(3)
104.5(2)
89.7(2)
98.5(2)
81.8(2)
O5–V1–O4
O5–V1–O3
O4–V1–O3
O6–V1–N3
O3–V1–N3
O12–V2–O10
O12–V2–O9
O10–V2–O9
O11–V2–N6
O9–V2–N6
101.7(3)
101.0(3)
149.1(2)
155.1(2)
74.4(2)
101.8(3)
101.5(2)
148.8(2)
154.8(2)
74.5(2)
Description of the Crystal Structure of (1)
Molecular structure and the atom numbering scheme for
complex (1) is depicted in Figure 1. Selected bond lengths
and angles are given in Table 3. The compound contains two
mononuclear vanadium molecules, one methanol molecule,
and one point two disordered water molecules. The coordina-
tion geometry around each vanadium atom can be described
as distorted square pyramidal with the tridentate aroylhydra-
zone ligand coordinated in a meridional fashion, forming
five- and six-membered chelate rings with bite angles of 74.4
(2)ꢀ (N3–V1–O3), 81.9(2)ꢀ (N3–V1–O4), 74.5(2)ꢀ (N6–V2–
O9), and 81.8(2)ꢀ (N6–V2–O10), typical for this type of
ligand system.[22,23] The aroylhydrazone ligands coordinate
in their dianionic enolate form, which is consistent with the
(2)
ꢀ
Bond lengths (A)
1.868(4)
V1–O1
V1–O5
V1–O7
V1–O2
V1–O6
V1–N1
1.966(4)
1.750(5)
2.134(5)
2.341(5)
1.572(5)
Bond angles (ꢀ)
observed C7–O3, C7–N2, C27–O9, and C27–N5 bond
ꢀ
O7–V1–O6
O6–V1–O1
O6–V1–O2
O7–V1–N1
O1–V1–N1
O7–V1–O5
O1–V1–O5
N1–V1–O5
103.8(2)
99.5(2)
97.3(2)
96.2(2)
83.6(2)
174.0(2)
83.1(2)
78.3(2)
O7–V1–O1
O7–V1–O2
O1–V1–O2
O6–V1–N1
O2–V1–N1
O6–V1–O5
O2–V1–O5
98.7(2)
98.0(2)
152.8(2)
159.0(2)
73.3(2)
81.4(2)
78.3(2)
lengths of 1.298(9), 1.316(9), 1.294(8), and 1.319(9) A in the
complex. The three donor atoms of the aroylhydrazone
ligand and the O atom of the deprotonated methanol ligand
define the basal plane of the square pyramidal coordination.
The apical position of the square pyramidal coordination is
occupied by the oxo group. The V atoms deviate from the
basal planes towardingꢀ the oxo groups by 0.375(2) A for V1
ꢀ
molecule and 0.383(2) A for V2 molecule.

120
Liu et al.
Fig. 2. Structure of complex (2) with the atom labeling scheme. All non-hydrogen atoms are represented at 30% probability thermal
ellipsoids.
angles are given in Table 3. The coordination geometry around and single crystal X-ray crystallographic measurements. The
the vanadium atom can be described as a distorted octahedral crystal structures of the complexes reveal that the V atoms
with the tridentate aroylhydrazone ligand coordinated in a are in distorted square pyramidal or octahedral coordination
meridional fashion, forming five- and six-membered chelate spheres. The vanadium complexes have interesting antibacte-
rings with bite angles of 73.3(2)ꢀ (N1–V1–O2) and 83.6(2)ꢀ rial activities on the strains B. subtilis, E. coli, and S. aureus.
(N1–V1–O1), typical for this type of ligand system.[22,23] The
aroylhydrazone ligand coordinates in its dianionic enolate
form, which is consistent with the observed C8–O2 and C8–N2
bond lengths of 1.292(7) and 1.302(8) A in the complex. The
Funding
ꢀ
three donor atoms of the aroylhydrazone ligand and the O
atom of the deprotonated methanol ligand define the equatorial
plane of the octahedral coordination. The axial positions of the
octahedral coordination are occupied by the oxo group and the
The authors are grateful to Hebei Key Laboratory of Bioi-
norganic Chemistry and College of Sciences of Agricultural
University of Hebei for financial support.
O atom of the methanol ligand. The V atom deviates from the
ꢀ
equatorial plane towarding the oxo groups by 0.315(2) A.
Supplemental Material
CCDC 934997 (1) and 934998 (2) contain the supplementary
crystallographic data for the complex. These data can be
obtained free of charge via http://www.ccdc.cam.ac.uk/
conts/retrieving.html, or from the Cambridge Crystallo-
graphic Data Centre, 12 Union Road, Cambridge CB2 1EZ,
UK; fax: (C44) 1223-336-033; or e-mail: deposit@ccdc.cam.
ac.uk.
Antibacterial Activities
The aroylhydrazone ligand H2La has weak activity against E.
coli, and no activity against B. subtilis and S. aureus. The
aroylhydrazone ligand H2Lb and the vanadium complexes
have weak to medium activities against the three strains. In
general, the vanadium complexes have stronger antibacterial
activities than the aroylhydrazone ligands. Complex (2) has
good activities against B. subtilis and S. aureus, with MIC
values of 1.56 and 3.13 mg mL¡1, respectively, which are
even close to the standard drugs penicillin and kanamycin.
Detailed comparison among the compounds can simply con-
clude that chloro-substitute groups of the benzene rings may
enhance the antibacterial activities of such compounds.
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