Synthesis, Structure, and Biological Property of New Vanadium Complex With Aroylhydrazone Ligand

Article abstract of DOI:10.1080/15533174.2014.900791

The aroylhydrazone Schiff base ligand [N'-(5-chloro-2-hydroxybenzylidene)-4-hydroxybenzohydrazide (H₂L) and salicylhydroxamic acid (Hsha) reacting with VO(acac)₂ in methanol gave the complex [VOL(sha)]·3H₂O. The complex wa

Full text of DOI:10.1080/15533174.2014.900791

Synthesis and Reactivity in Inorganic, Metal-Organic, and
Nano-Metal Chemistry
ISSN: 1553-3174 (Print) 1553-3182 (Online) Journal homepage: http://www.tandfonline.com/loi/lsrt20
Synthesis, Structure, and Biological Property of
New Vanadium Complex With Aroylhydrazone
Ligand
Chao Li, Yan-Li Dong, Xu-Feng Meng, Xin Zhou & Jing-Jun Ma
To cite this article: Chao Li, Yan-Li Dong, Xu-Feng Meng, Xin Zhou & Jing-Jun Ma (2016)
Synthesis, Structure, and Biological Property of New Vanadium Complex With Aroylhydrazone
Ligand, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 46:1,
118-122, DOI: 10.1080/15533174.2014.900791
To link to this article: http://dx.doi.org/10.1080/15533174.2014.900791
Accepted author version posted online: 03
Feb 2015.
Submit your article to this journal
Article views: 45
View related articles
View Crossmark data
Full Terms & Conditions of access and use can be found at
http://www.tandfonline.com/action/journalInformation?journalCode=lsrt20
Download by: [Orta Dogu Teknik Universitesi]
Date: 15 February 2016, At: 06:33

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry (2016) 46, 118–122
Copyright © Taylor & Francis Group, LLC
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2014.900791
Synthesis, Structure, and Biological Property of New
Vanadium Complex With Aroylhydrazone Ligand
CHAO LI, YAN-LI DONG, XU-FENG MENG, XIN ZHOU, and JING-JUN MA
College of Sciences, Agricultural University of Hebei, Baoding, P. R. China
Received 4 November 2013; accepted 25 February 2014
The aroylhydrazone Schiff base ligand [N’-(5-chloro-2-hydroxybenzylidene)-4-hydroxybenzohydrazide (H2L) and salicylhydroxamic
acid (Hsha) reacting with VO(acac)2 in methanol gave the complex [VOL(sha)]¢3H2O. The complex was characterized by elemental
analyses and IR spectroscopic method in the solid state. Single crystal X-ray analysis was performed, which indicated that the
complex is a mononuclear compound. The V atom in the complex is in an octahedral geometry. VIV in VO(acac)2 was oxidized to
VV in the complex by aerial oxygen during the synthesis and crystallization. Thermal behavior of the complex was studied.
Antibacterial activity of the aroylhydrazone ligand and the complex has been studied on the bacteria strains B. subtilis, E. coli, and
S. aureus.
Keywords: vanadium complex, crystal structure, aroylhydrazone, antibacterial property
Introduction
([VO(acac)2]) were purchased from Merck and Fluka, and
used as received. The aroylhydrazone Schiff base ligand H2L
The presence of vanadium(IV) and vanadium(V) compounds was prepared in over 90% yield by condensation reaction of
in many vanadium-dependent enzymes, for instance, nitroge- 5-chlorosalicylaldehyde with 4-hydroxybenzohydrazide in
nases and haloperoxidases,[1–3] as well as insulin mimick- methanolic media, according to the literature method.[16,17]
ing,[4,5] have stimulated the search for structural and All other chemicals and solvents used in this work were of
functional models based on vanadium complexes. Moreover, analytical grade available commercially and used without
oxovanadium complexes have been attracted tremendous further purification. Elemental analyses (carbon, hydrogen
attention for their versatile catalytic properties in organic and nitrogen) of the compounds were obtained from a Carlo
synthesis.[6–8] In recent years, the remarkable biological activ- ERBA Model EA 1108 analyzer. Infrared spectra were col-
ity of aroylhydrazones and the dependence of their mode of lected by using KBr pellets on a Jasco-5300 FT-IR spectro-
chelation with transition metal ions in living systems have photometer. Solution electrical conductivity was measured
been of significant interest.[9–12] Vanadium complexes of with a DDS-11A conductivity meter. Thermal analysis of the
aroylhydrazones have also been reported to possess various complex was carried out by heating at a rate of 10ꢀC per min-
antimicrobial activities.[13–15] Aiming at obtaining new vana- ute on a Perkin Elmer TGA-4000 thermo balance.
dium complexes with biological properties, in this study, a
new vanadium complex, [VOL(sha)]¢3H2O, where L is the
dianionic species of [N0-(5-chloro-2-hydroxybenzylidene)-4-
hydroxybenzohydrazide (H2L), and sha is the monoanionic
species of salicylhydroxamic acid (Hsha), was synthesized,
characterized, and studied for its activity against B. subtilis,
E. coli, and S. aureus.
Synthesis of [VOL(sha)]¢3H2O
[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 H2L (0.01 mol, 2.90 g). The mixture was gently
refluxed for 2 h, then most of the solvent was evaporated by
distillation. After cooling, the resulting brown solid was fil-
tered off, washed with cold methanol, and dried in a vacuum
containing anhydrous CaCl2. Yield: 3.35 g (62%). Anal.
Calcd. for C42H42Cl2N6O17V2 (%): C, 46.90; H, 3.94; N,
Experimental
Materials and Methods
7.81. Found: C, 46.73; H, 3.82; N, 7.93. IR data (cm¡1
,
5-Chlorosalicylaldehyde, 4-hydroxybenzohydrazide, salicyl-
hydroxamic acid, and vanadium(IV) oxide acetylacetonate
KBr): 3451 (br, m), 3213 (w), 1605 (vs), 1543 (w), 1493 (m),
1382 (m), 1265 (m), 1146 (w), 1115 (w), 966 (m), 917 (w), 818
(w), 732 (w), 656 (w), 588 (m), 576 (m), 483 (w), 464 (w), 445
(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.
Address correspondence to Jing-Jun Ma, College of Sciences,
Agricultural University of Hebei, Baoding 071001, P. R. China.
E-mail: majingjun71@126.com

New Vanadium Complex With Aroylhydrazone Ligand
119
X-Ray Crystallography
pounds 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) containing 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 tempera-
ture, the optical density 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 3.
A suitable X-ray quality crystal of the complex was pick up
under a microscope and investigated in a diffraction experi-
ment at 298(2) K on a Bruker Apex II diffractometer with
monochromated Mo Ka radiation (λ D 0.71073 A) obtained
from a graded multilayer X-ray optics. The structure was
solved by direct methods with SHELXS-97,[18] and refined
with full-matrix least-squares techniques on F2 with
SHELXL-97.[18] The C- and O6-bonded hydrogen atoms
ꢀ
were calculated in an idealized geometry, riding on their par-
ꢀ
ent atoms, with distances restrained to 0.93–0.96 A for C–H
ꢀ
and 0.82 A for O–H. The water and amino hydrogen atoms
were located from a difference Fourier map and refined iso-
tropically, with O–H, H¢¢¢H, and N–H distances restrained
ꢀ
to 0.85(1), 1.37(2), and 0.90(1) A, respectively. The crystal
data and refinement parameters are listed in Table 1.
Results and Discussion
Synthesis and Characterization
Antibacterial Assay
Reaction of VO(acac)2 with the tridentate aroylhydrazone
ligand H2L and salicylhydroxamic acid in methanol under
aerobic conditions afforded the neutral oxovanadium(V)
complex. Most likely during the synthesis and crystallization
of the complex from oxovanadium(IV) starting material, the
aerial oxygen acts as the oxidizing agent. Elemental analyses
of the complex are in consistent with the general molecular
formula proposed by single-crystal X-ray determination. In
absolute methanolic solution, it is electrically nonconducting.
The antibacterial activity was 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
bromide].[19] A stock solution of the synthesized compound
(50 mg mL¡1) in DMSO was prepared and quantities of the
test compounds were incorporated in specified quantity of
sterilized liquid Mueller-Hinton medium. A specified quan-
tity 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 com-
IR Spectroscopic Characteristics
Infrared spectra of the free aroylhydrazone ligand and the
complex gave information about the coordination. Both the
free ligand and the complex display broad bands in the region
3400–3480 cm¡1 and weak and sharp bands in the region
3210–3240 cm¡1. These bands are possibly due to the O–H
and N–H stretches. The absence of the n(CDO) band, which
presents in the free aroylhydrazone ligand at 1657 cm¡1, indi-
cates the enolization of the amide functionality upon coordi-
nation to the V atom. A very strong band observed at
Table 1. Crystallographic data for the complex
Chemical formula
Formula weight
Crystal system
C42H42Cl2N6O17V2
1075.6
Triclinic
Space group
P-1
Unꢀit cell dimensions
a (A)
10.2597(6)
10.6524(6)
12.0500(7)
111.469(1)
95.724(1)
90.194(1)
1218.3(1)
1
1605 cm¡1 for the complex can be attributed to the stretching
ꢀ
b (A)
[20]
ꢀ
vibration of the azomethine group, nCDN
.
The spectra of
c (A)
a (ꢀ)
b (ꢀ)
the complex displays typical and medium band at 966 cm¡1
which is assigned to the stretches of the VDO bond.[21]
g (ꢀ)
ꢀ
V (A3)
Z
Description of the Crystal Structure of the Complex
r (g cm¡3
)
1.466
0.569
Molecular structure and the atom numbering scheme for the
complex is depicted in Figure 1. Selected bond lengths and
angles are given in Table 2. The compound contains a mono-
nuclear vanadium molecule and three water molecules. The
coordination geometry around the vanadium atom can be
described as a distorted octahedral with the tridentate aroyl-
hydrazone ligand coordinated in a meridional fashion, form-
ing five- and six-membered chelate rings with bite angles of
74.2(1)ꢀ (N1–V1–O2) and 83.6(1)ꢀ (N1–V1–O1), typical for
this type of ligand system.[22,23] The aroylhydrazone ligand
coordinates in its dianionic enolate form, which is consistent
m (mm¡1
)
Tmin, Tmax
0.8478, 0.8615
6909
4956
3764
350
Reflections collected
Reflections unique
Reflections observed [I > 2s(I)]
Parameters
Restraints
11
R1, wR2 [I > 2s(I)]
R1, wR2 (all data)
Goodness-of-fit on F2
0.0413, 0.1018
0.0621, 0.1152
1.038

120
Li et al.
ꢀ
Table 2. Selected bond lengths (A) and angles (ꢀ) for the complex
ꢀ
Bond lengths (A)
V1–O1
V1–O5
V1–N1
1.8589(18)
1.8722(16)
2.0965(19)
V1–O2
V1–O7
V1–O4
1.9539(16)
1.5875(19)
2.1687(18)
Bond angles (ꢀ)
O7–V1–O1
O1–V1–O5
O1–V1–O2
O7–V1–N1
O5–V1–N1
O7–V1–O4
O5–V1–O4
N1–V1–O4
99.70(10)
108.74(8)
149.58(8)
94.68(8)
165.87(7)
165.11(8)
75.59(7)
O7–V1–O5
O7–V1–O2
O5–V1–O2
O1–V1–N1
O2–V1–N1
O1–V1–O4
O2–V1–O4
90.05(8)
102.52(9)
91.83(7)
83.60(8)
74.16(7)
81.60(8)
82.21(7)
100.20(7)
with the observedꢀ C8–O3 and C8–N2 bond lengths of 1.304
(3) and 1.310(3) A in the complex. The salicylhydroxamate
ligand coordinates to the vanadium atom through the car-
bonyl O atom and the hydroxamate O atom. The three donor
atoms of the aroylhydrazone ligand and the hydroxamate O
Fig. 1. Molecular structure of the complex with the atom labeling
scheme. All non-hydrogen atoms are represented at 30% proba-
bility thermal ellipsoids.
ꢀ
atom of salicylhydroxamate ligand define the equatorial H8A¢¢¢O10iii [O8–H8A D 0.81(1) A, H8A¢¢¢O10iii D 2.06(2)
ꢀ
ꢀ
plane of the octahedral coordination. The axial positions of A, O8¢¢¢O10iii D 2.793(9) A, O8–H8A¢¢¢O10iii D 150(4)ꢀ], to
the octahedral coordination are occupied by the oxo group form 1D chains (Figure 2).
and the carbonyl O atom of the salicylhydroxamate ligand.
The V atom deviates from the equatorial plane toward the
oxo group by 0.212(2) A.
ꢀ
Thermal Behavior
In the crystal packing structure, two oxovanadium(V)
Thermogravimetric analysis of the complex was carried out
complex molecules are linked through intermolecular N3–
in the temperature range 50–1000ꢀC at a heating rate of 10ꢀC
ꢀ
H3A¢¢¢O2i hydrogen bonds [N3–H3A
D
0.90(1) A,
min¡1. The TG curve of the complex is given following deg-
radation scheme (Figure 3). The complex decomposes from
50 to 90ꢀC, which is caused by the removal of the water mole-
cules. Above this temperature, the TG curve shows two steps
of weigh losses. The first step of decomposition in the temper-
ature range 90–465ꢀC involved the removal of the hydroxa-
mate ligand. The second step of decomposition in the
temperature range 465–498ꢀC involved the removal of the
aroylhydrazone ligand, and the formation of the final product
V2O5. The observed residue of 16.8% agrees well with the cal-
culated value of 16.7%.
ꢀ
ꢀ
H3A¢¢¢O2i D 2.19(2) A, N3¢¢¢O2i D 2.928(3) A, N3–
H3A¢¢¢O2i D 139(3)ꢀ, symmetry code for i: 1 – x, – y, 1 – z],
to form a dimer. The dimers are further linkeꢀd via hydrogen
bonds of N3–H3A¢¢¢O6 [N3–H3A D 0.90(1) A, H3A¢¢¢O6 D
ꢀ
ꢀ
2.02(3) A, N3¢¢¢O6 D 2.611(3) A, N3–H3A¢¢¢O6 D 122(3)ꢀ],
ꢀ
ꢀ
O6–H6¢¢¢N2 [O6–H6 D 0.82 A, H6¢¢¢N2 D 1.94 A, O6¢¢¢N2
ꢀ
D 2.735(2) ꢀA, O6–H6¢¢¢N2 D 165ꢀ], ꢀO8–H8B¢¢¢O8ii [O8–H8B
ꢀ
D 0.85(1) A, H8B¢¢¢O8ii D 2.07(3) A, O8¢¢¢O8ii D 2.76(1) A,
O8–H8B¢¢¢O8ii D 139(4)ꢀ, symmetry code for ii: 1 – x, – y, –
ꢀ
z], O9–H9B¢¢¢O10iii [O9–H9B D 0.85(1) A, H9B¢¢¢O10iii
D
ꢀ
ꢀ
2.44(4) A, O9¢¢¢O10iii D 2.845(8) A, O9–H9B¢¢¢O10iii D 111
(3)ꢀ, symmetry code for iii: 1 – x,ꢀ 1 – y, 1 – z], O10–
H10A¢¢¢O8iii [O10–H10A D 0.8ꢀ5(1) A, H10A¢¢¢O8iii D 2.03
ꢀ
(2) A, O10¢¢¢O8iii D 2.793(9) A, O10–H10A¢¢¢O8iii D 151
ꢀ
(ꢀ4)ꢀ], O3–H3¢¢¢O3iv [O3–H3 D 0.82(1) A, H3¢¢¢O3iv D 2.05(2)
ꢀ
A, O3¢¢¢O3iv D 2.798(4) A, O3–H3¢¢¢O3iv D 152(3)ꢀ, symme-
try code for iv: –ꢀ x, 1 – y, 2 – z], O10–H10B¢¢¢O9iii [O10–
ꢀ
H10B D 0.85(1) A, H10B¢¢¢O9iii D 2.03(2) A, O10¢¢¢O9iii
D
ꢀ
2.845(8) A, O10–H10B¢¢¢O9iii
D
160(3)ꢀ], and O8–
Table 3. MIC values (mg mL¡1) of the tested compounds
B. subtilis
E. coli
S. aureus
H2L
12.5
6.25
0.78
0.39
>100
25
>100
6.25
12.5
12.5
3.13
1.56
The complex
Penicillin
Kanamycin
Fig. 2. Packing structure of the complex. Hydrogen bonds are
shown as thin dashed lines.

New Vanadium Complex With Aroylhydrazone Ligand
121
html, or from the Cambridge Crystallographic Data Centre,
12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44)
1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk.
References
1. Hu, Y.-L.; Lee, C. C.; Ribbe, M. W. Extending the carbon chain:
Hydrocarbon formation catalyzed by vanadium/molybdenum
nitrogenases. Science 2011, 333, 753–755.
2. Hu, Y.-L.; Lee, C. C.; Ribbe, M. W. Vanadium nitrogenase: A two-
hit wonder? Dalton Trans. 2012, 41, 1118–1127.
3. Mba, M.; Pontini, M.; Lovat, S.; Zonta, C.; Bernardinelli, G.; Kun-
dig, P. E.; Licini, G. C3 vanadium(V) amine triphenolate com-
plexes: Vanadium haloperoxidase structural and functional models.
Inorg. Chem. 2008, 47, 8616–8618.
4. Mukherjee, T.; Pessoa, J. C.; Kumar, A.; Sarkar, A. R. Synthesis,
spectroscopic characterization, insulin-enhancment, and competi-
tive DNA binding activity of a new Zn(II) complex with a vitamin
B-6 derivative-a new fluorescence probe for Zn(II). Dalton Trans.
2012, 47, 5260–5271.
Fig. 3. DT curve of the complex.
5. Crans, D. C.; Trujillo, A. M.; Pharazyn, P. S.; Cohen, M. D. How
environment affects drug activity: Localization, compartmentaliza-
tion and reactions of a vanadium insulin-enhancing compound,
dipicolinatooxovanadium(V). Coord. Chem. Rev. 2011, 255, 2178–
2192.
6. Grivani, G.; Khalaji, A. D.; Tahmasebi, V.; Gotoh, K.; Ishida, H.
Synthesis, characterization and crystal structures of new bidentate
Schiff base ligand and its vanadium(IV) complex: The catalytic
activity of vanadyl complex in epoxidation of alkenes. Polyhedron
2012, 31, 265–271.
7. Romanowski, G.; Wera, M. Mononuclear and dinuclear chiral
vanadium(V) complexes with tridentate Schiff bases derived from R
(¡)-1,2-diaminopropane: Synthesis, structure, characterization and
catalytic properties. Polyhedron 2010, 29, 2747–2754.
8. Orabi, A. S.; Ayad, M. I.; Ramadan, A. E. M. Synthesis, character-
ization and oxidase catalytic activity of vanadium(IV) and oxova-
nadium(IV) complexes with Schiff base ligands derived from beta-
diketones. Transition Met. Chem. 1998, 23, 391–396.
9. Blanot, D.; Lee, J.; Girardin, S. E. Synthesis and biological evalua-
tion of biotinyl hydrazone derivatives of muramyl peptides. Chem.
Biol. Drug Des. 2012, 79, 2–8.
10. Zhang, M.; Xian, D.-M.; Li, H.-H.; Zhang, J.-C.; You, Z.-L. Syn-
thesis and structures of halo-substituted aroylhydrazones with anti-
microbial activity. Aust. J. Chem. 2012, 65, 343–350.
11. Horiuchi, T.; Takeda, Y.; Haginoya, N.; Miyazaki, M.; Nagata,
M.; Kitagawa, M.; Akahane, K.; Uoto, K.. Discovery of novel
thieno[2,3-d]pyrimidin-4-yl hydrazone-based cyclin-dependent
kinase 4 inhibitors: Synthesis, biological evaluation and structure-
activity relationships. Chem. Pharm. Bull. 2011, 59, 991–1002.
12. Kaplancikli, Z. A.; Altintop, M. D.; Ozdemir, A.; Turan-Zitouni,
G.; Khan, S. I.; Tabanca, N. Synthesis and biological evaluation of
some hydrazone derivatives as anti-inflammatory agents. Lett.
Drug Des. Discov. 2012, 9, 310–315.
13. Wazalwar, S. S.; Bhave, N. S.; Dikundwar, A. G.; Ali, P. Micro-
wave assisted synthesis and antimicrobial study of Schiff base vana-
dium(IV) complexes of phenyl esters of amino acids. Synth. React.
Inorg. Met.-Org. Nano-Met. Chem. 2011, 41, 459–464.
Antibacterial Activities
Hydrazone compounds and their complexes have been widely
studied for their interesting antibacterial activities. In the
present work, the aroylhydrazone ligand H2L has weak activ-
ity against B. subtilis and S. aureus, and no activity against E.
coli. The complex, derived from H2L and Hsha, has stronger
activities against B. subtilis and E. coli, but similar activity
against S. aureus, when compared to H2L. In general, the
antibacterial activity of the complex is not so good. Since
vanadium complexes play an important role in biological sys-
tems, much work needs to be done to explore more potent
antibacterial material based on vanadium.
Conclusions
A new oxovanadium(V) complex was synthesized and char-
acterized with the help of microanalytical, IR spectroscopic,
and single-crystal X-ray crystallographic measurements. The
crystal structure of the complex reveals that the V atom is in
distorted octahedral coordination sphere. Thermal behavior
of the complex was studied. The vanadium complex has
medium antibacterial activity on the bacteria strains B. subti-
lis, E. coli, and S. aureus, which is similar to those reported
previously.[24–26]
Funding
The authors are grateful to the Hebei Key Laboratory of Bio-
inorganic Chemistry and College of Sciences of Agricultural
University of Hebei for financial support.
14. Shahzadi, S.; Ali, S.; Parvez, M.; Badshah, A.; Ahmed, E.; Malik,
A. Synthesis, spectroscopy and antimicrobial activity of vanadium
(III) and vanadium(IV) complexes involving Schiff bases derived
from tranexamic acid and X-ray structure of zwitter ion of tranexa-
mic acid. Russ. J. Inorg. Chem. 2007, 52, 386–393.
Supplementary Material
15. Sharma, N.; Thakur, M.; Chaudhry, S. C. Synthesis, characteriza-
tion, electrochemical study, and antimicrobial activity of bis(ben-
zoylacetonato) vanadium(IV) complexes of biphenylphenols. J.
Coord. Chem. 2010, 63, 1228–1238.
CCDC 969433 contains the supplementary crystallographic
data for the complex. The data can be obtained free
of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.

122
Li et al.
16. Liu, W.-H.; Song, S.-J.; Ma, J.-J. N’-(5-Bromo-2-hydroxybenzyli- 22. Li, Z.-P.; Li, Y.-J.; Li, Z.-X.; Li, H.; Xiao, Z.-P. Synthesis and crys-
dene)-4-nitrobenzohydrazide methanol monosolvate. Acta Crystal-
logr. 2011, E67, o2198.
17. Zhou, X.; Ma, J.-J. Synthesis, characterization and crystal struc-
tures of 2-cyano-N’-(2-chlorobenzylidene)acetohydrazide and
2-cyano-N’-(4-dimethylaminobenzylidene)acetohydrazide. J. Chem.
Crystallogr. 2012, 42, 1138–1141.
18. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr.
2008, A64, 112–122.
19. Meletiadis, J.; Meis, J. F. G. M.; Mouton, J. W.; Donnelly, J.
tal structures of N’-3,5-dibromo-2-hydroxybenzylidene)-2-hydroxy-
3-methylbenzohydrazide and its oxovanadium(V) complex [N’-(3,5-
dibromo-2-oxidobenzylidene-kO)-2-hydroxy-3-methylbenzohydra-
zidato-k2N’,O](methanol-kO)(methanolato-kO)oxidovanadium(V).
J. Chem. Crystallogr. 2011, 41, 1568–1572.
23. Lalami, N. A.; Monfared, H. H.; Noei, H.; Mayer, P. Binuclear
vanadium(V) complexes of bis(aryl)adipohydrazone: Synthesis,
spectroscopic studies, crystal structure and catalytic activity. Transi-
tion Met. Chem. 2011, 36, 669–677.
P.; Verweij, P. E. Comparison of NCCLS and 3-(4,5-dimethyl- 24. Zhang, W.-G.; Liang, J.-H. Microwave-assisted synthesis, crystal
2-thiazyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) methods
of in vitro susceptibility testing of filamentous fungi and devel-
opment of a new simplified method. J. Clin. Microbiol. 2000,
38, 2949–2954.
structures, and in vitro antibacterial studies of cobalt(III) and vana-
dium(V) complexes derived from N,N’-1,2-propylene-bis(3-methyl-
salicylideneimine). Synth. React. Inorg. Met.-Org. Nano-Met.
Chem. 2013, 43, 1355–1360.
20. Sarkar, A.; Pal, S. Some ternary complexes of oxovanadium(IV) 25. Pawar, V.; Joshi, S.; Uma, V. Antibacterial and antioxidant proper-
with acetylacetone and N-(2-pyridyl)-N’-(salicylidene)hydrazine
and its derivatives. Polyhedron 2006, 25, 1689–1694.
ties of macrocyclic Schiff bases with vanadium(V) complexes. Asian
J. Chem. 2013, 25, 1497–1500.
21. Sarkar, A.; Pal, S. Complexes of oxomethoxovanadium(V) with tri- 26. Sharma, N.; Kumari, M.; Kumar, V.; Chaudhry, S. C.; Kanwar, S. S.
dentate thiobenzhydrazide based Schiff bases. Inorg. Chim. Acta
2008, 361, 2296–2304.
Synthesis, characterization, and antibacterial activity of vanadium(IV)
complexes of hydroxamic acids. J. Coord. Chem. 2010, 63, 176–184.