FULL PAPER

DOI: 10.1002/cjoc. 201100153

Synthesis, Characterization and Antimicrobial Activity of

Oxovanadium(IV) Complexes of Schiff Base Hydrazones
Containing Quinoxaline Moiety

Lakshmi, P. V. Anantha*,a Satyanarayana, T.b Reddy, P. Sarithaa

a
Department of Chemistry, University College for Women, Osmania University, Hyderabad, India
b
O U P G College, Osmania University, Mirzapur, India

The oxovanadium(IV) complexes of the Schiff base hydrazones, synthesized from 3-hydrazinoquinoxaline-2-
one (HQO) with salicylaldehyde (HSHQO), o-hydroxyacetophenone (HHAHQO), dehydroacetic acid (HDHAHQO)
and o-nitrobenzaldehyde (NBHQO) were synthesized and characterized on the basis of analytical, conductance,
magnetic moment, infrared, NMR, ESR and electronic spectral data. The ligands HSHQO, HDHAHQO behaved as
monobasic tridentate ONN donors through phenolic oxygen, azomethine nitrogens. The ligand HAHQO acted as a
monobasic bidentate ON donor through the phenolic oxygen, azomethine (free) nitrogen and the ligand NBHQO
acted as neutral bidentate ON donor through oxygen of the nitro group and azomethine (free) nitrogen.

Keywords oxovanadium(IV), hydrazones, ONN donor, ON donor

Introduction species with hydrazones having pharmacological activ-

Quinoxalines are an important class of nitrogen-
containing heterocycles with a variety of biological ac-
tivities, specifically as AMPA/GlyN receptor antago-
nists,[1-3] angiotensin II receptor antagonists,[4,5] anti-
cancer agents,[6] anti-infection agents[7] and immuno-
modulating agents.[8] Metal complexes of quinoxaline
derivatives, particularly those having azomethine cen-
ters of coordination, have received attention because of
their potential metal binding properties and promising
applicabilities.[9,10] Importance was hence given to
studying these systems in our laboratories.[11-17]
Interest in the study of Schiff base hydrazones has
ity is of growing interest.
In view of the importance of such oxovanadium(IV)
complexes of hydrazones, we describe here the synthe-
sis, characterization and antimicrobial activity of
oxovanadium(IV) complexes of HSHQO, HHAHQO,
HDHAHQO and NBHQO.
Experimental
General
All the chemicals used were either of AR or chemi-
cally pure grade. IR spectra were recorded using KBr
discs in the 4000—400 cm 1 region on a Schimadzu
－

been growing because of their antimicrobial, anti-tu- IR-435 and in Nujol media in the 4000—200 cm 1 re-
－

berculosis, and anti-tumor activity.[18-23] Schiff bases
play an important role in inorganic chemistry, as they
easily form stable complexes with most transition metal
ions. The development of the field of bioinorganic
chemistry has increased the interest in Schiff base com-
plexes, since it has been recognized that many of these
complexes may serve as models for biologically impor-
tant species.[18-20]
Vanadium chemistry has attracted attention due to its
interesting structural features[24] and biological rele-
vance. The biochemical aspects of vanadium complexes
have further promoted the coordination chemistry of
vanadium.[25] Oxovanadium complexes have potential
applications such as anti-diabetic,[26,27] antibacterial and
gion on a Perkin-Elmer 283-B spectrometer and elec-
tronic spectra of solids were recorded on a Cary-2390
UV-Vis-NIR spectrophotometer. The elemental analysis
was carried out using Heraus-CHN-rapid analyzer. The
1
H NMR spectra are recorded on Bruker-400 MHz
spectrometer in DMSO-d6 solvent. Metal contents were
estimated using an AAS Perkin Elmer-2380. Magnetic
susceptibilities of complexes were measured on a Fara-
day balance CAHN-7550-03 USA at room temperature
using Hg[Co(NCS)4] as calibrant. Diamagnetic correc-
tions using Pascal’s constants and temperature inde-
pendent paramagnetic corrections were computed.[30]
The electrical conductance measurements were recorded
using 10 3 molar solutions in DMSO with an Elico con-
－

antifungal.[28,29] The interaction of simple vanadium ductivity bridge (Model CM-180) and dip type cell

* E-mail: ananthaprasad2003@yahoo.co.in
Received July 21, 2011; accepted September 15, 2011; published online February 29, 2012.

Chin. J. Chem. 2012, 30, 935—940 © 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 935
FULL PAPER
calibrated with KCl solutions. DTA was carried out us-
ing a Lead and Northup-USA instrument and TGA on a
Perkin-Elmer model TGS-2 instrument. EPR was re-
corded on Jeol SE-3Xspectrometer at r.t. and liquid ni-
trogen temperature.
Synthesis of the ligands
The ligands were synthesized by condensing
3-hydrazinoquinoxaline-2-one[31] with salicyladehyde,
o-hydroxyacetophenone, and dehydroacetic acid and
o-nitrobenzaldehyde. They were prepared, characterized
(Figure 1) and reported from our laboratory.[12,15,16]
H H
N O N O
N NH N NH
N N
HO HO
HSHQO HHAHQO
H
N O
N NH H but soluble in dimethyl sulfoxide and dimethyl forma-
CH3 N O O2N
N O
N
HO O
N N
H
NBHQO
CH3
HDHAHQO
Figure 1 Proposed structures of ligands.
Synthesis of the complexes
A general method was adopted for the preparation of
all the complexes. A methanolic suspension of the
ligand was added in small increments to a methanolic
solution of the metal chloride. After complete addition
of the metal to ligand, mole ratio was always kept as
1∶2. It was observed that the ligand dissolved com-
pletely in the presence of metal ion and a clear solution
was obtained after each addition. The pH of the reaction
mixture was then raised to 7 using a 1% alcoholic am-
monia solution. The reaction mixture was refluxed for 4
h. The colored product obtained was filtered hot and
washed successively with small increments of methanol,
petroleum ether and ether and dried in vacuo.
Pharmacology
The Schiff bases and their complexes were evaluated
for antimicrobial activity against one strain Gram＋ve
bacteria (Staphylococcus aureus), Gram－ve bacteria
(Escherichia coli). Medium used was nutrient agar. It
contained (g/L), (10) peptone, (10) beef extract, (5)
NaCl, (15) agar. The medium was sterilized by auto-
claving at 121 ℃ for 15 min, then cooled to 55 ℃
and poured into sterile 4”petriplates (20 mL) kept on an
even surface and allowed to solidify. Exponentially
growing cultures (18 h old) were taken and seeded onto
the nutrient agar plates by spread plate technique. 1 mL
of the culture was placed onto the nutrient agar plate
936 www.cjc.wiley-vch.de © 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Lakshmi, Satyanarayana & Reddy
and the culture was spread all over the plate using a
sterile spreader and was allowed to dry. Filter paper
discs of 6 mm diameter were prepared from Whatman
No 1 filter paper and sterilized by autoclaving at 121 ℃
for 15 min and were dried in hot air oven. DMSO solu-
tions containing ligand and metal complexes in varied
concentrations (100, 10 and 1 mg/L) were absorbed
onto each disc. The discs were placed at a distance of
2.5 cm from each other on the surface of the inoculated
media plates. The plates were then kept in the refrigera-
tor for 1 h to allow the diffusion of the compound into
the medium and later were placed in the incubator. They
were incubated at 37 ℃ for 18 h. After the incubation
period, the results were noted. Presence of a zone of
CH3
inhibition around a particular disc indicates antibacterial
activity of that compound. The experiments were re-
peated three times to obtain consistent results.
Results and Discussion
All the complexes are colored and stable in atmos-
phere. They are insoluble in common organic solvents
mide. The analytical data and proposed formulae for the
complexes are given in Table 1. Analytical data indicate
that the metal to ligand stoichiometry is 1∶1 in the
complexes of HSHQO, HDHAHQO and 1∶2 in the
complexes of HHAHQO, NBHQO. The data also pro-
vide evidence for sulphate in all the complexes except
the complex of HHAHQO. All the complexes are
non-electrolytes. Hence the sulphate is in coordination
sphere. All the complexes possess a room temperature
magnetic moment value in the range of 1.82—1.89
which is well within the range of the magnetic moment
expected for the presence of one unpaired electron.[32,33]
Proton of phenolic OH group which was observed at δ
11.8, 13.1 and 13.1 in 1H NMR of the ligands, HSHQO,
HDHAHQO and HHAHQO, has disappeared in com-
plexes (Figure 2), indicating coordination of the
phenoxide ion via deprotonation. Characteristic infra
red frequencies of ligands and complexes are given in
Table 2.
Figure 2 1
H NMR spectrum of [VO(HAHQO)2].
Chin. J. Chem. 2012, 30, 935—940
Synthesis, Characterization and Antimicrobial Activity of Oxovanadium(IV) Complexes

Table 1 Analytical data of ligands and complexes

Calcd. (Found)/%
Ligand/Complex with molecular formula
Metal Carbon Hydrogen Nitrogen Sulphur
HSHQO 64.44 4.28 20.00
C15H12N2O2 (64.42) (4.15) (20.44)
[(VO)2(SHQO)2SO4] 12.94 45.68 2.79 14.21 4.06
(V2C30H22N8O8S) (12.53) (44.89) (2.78) (14.04) (4.03)
HHAHQO 65.30 4.76 19.04
C16H14N2O2 (65.30) (4.87) (19.23)
[VO(HAHQO)2] 7.81 58.80 3.88 17.15
(VC32H26N8O5) (7.68) (57.73) (3.93) (16.84)
HDHAHQO 58.89 4.29 17.17
C16H14N4O4 (56.86) (4.01) (16.84)
[(VO)2(DHAHQO)2SO4] 11.59 43.64 2.95 12.73 3.64
(V2C32H26N8O14S) (11.38) (42.83) (2.94) (12.52) (3.59)
NBHQO 58.25 3.56 22.65
C15H11N5O2 (58.14) (3.47) (22.50)
[VO(NBHQO)2SO4] 6.53 46.09 2.82 17.93 4.09
(VC30H22N10O11S) (6.41) (45.21) (2.80) (17.57) (4.01)

Table 2 Characteristic infra red frequencies of ligands and complexes (cm－1)

ν(ΝΗ ) ν(C＝O) ν(C＝O) ν(C＝N) ν(C＝N) ν(C—O)
Compound ν(ΟΗ) ν(ΝΗ) ν(NO2) ν(NO2) New Bands
(ring) (lactone) (lactam) (free) (ring)
HSHQO 3050 3150 2900 1690 1600 1580 1346
1120, 1080, 1040,
[(VO)2(SHQO)2SO4] — 3250 3000 1690 1550 1525 1360
980, 620
HHAHQO 3000—2850 1680 1612 1560 1210
[VO(HAHQO)2] — 3200 3000 1680 1600 1560 1240 940, 590, 550, 530
HDHAHQO 3000 3350 2850 1680 1670 1596 1540 1395
1100—1140, 1030,
[(VO)2(DHAHQO)2SO4] — 3350 2850 1680 1670 1570 1520 1415
640, 600, 540, 450
NBHQO 3300 2950—2850 1674 1540 1520 1560 1350
1120, 1030, 920, 640,
[VO(NBHQO)2SO4] 3300 3000 1680 1520 1580 1330
580, 540, 490, 465

Characterization of [(VO)2(SHQO)2SO4] ometry.[37]

The downward shifts in ν(C＝N)(ring), ν(C＝N)(exo) Characterization of [VO(HAHQO)2]
and upward shifts in ν(C—Ο), ν(N—N) in IR spectrum
The downward shifts in ν(C＝N)(exo) and upward
indicate binding of the ligand through an ONN sequence
shifts in ν(C—Ο), ν(N—N) in IR spectrum indicate
involving phenolic oxygen and azomethine nitrogens.[34]
binding of the ligand through an ON sequence involving
No band is observed at 3050 cm 1, which is present in
－

phenolic oxygen and one of the azomethine nitrogens. A

the ligand, suggesting the cleavage of intramolecular
broad strong band in the region of 3000—2850 cm 1
－

hydrogen bonded —OH with subsequent deprotonation
and coordination through phenolic oxygen. The stretch-
ing frequency attributed to ν(N—H) around 3150 cm 1
－
in the free ligand is observed at 3250—3200 cm 1 due
－
to the cleavage of intramolecular hydrogen bonding.[35]
has been attributed to a combination of intramolecular
hydrogen bonded ν(N—H) and ν(O—H) in the spec-
trum of the free ligand. ν(N—H)(ring) also appears in
the same region. Instead of this band, the IR spectrum of
complex shows a characteristic band at 3200 cm 1
－

A strong non-ligand band, observed at 980 cm 1, is as-

－

[36]
which can be attributed to ν(N—H) of side chain. Dur-
signed to ν(V＝O). The four non-ligand bands ap- ing complexation the hydrogen bond gets severed and as
pearing in the region 1080—1120, 1040 and 620 cm 1
－

[36]
can be attributed to bidentate sulphate (bridging). The
new bands in the far IR region are attributed to ν(M—
such ν(N—H) is shifted to higher frequency. ν(N—
H)(ring) appears as a weak absorption band at 3000
cm 1. As the complex is isolated from neutral medium,
－

N), ν(M—O). Electronic spectrum shows three bands at the deprotonation of phenolic group is the reasonable
17241, 19230 and 25641 cm 1, which are assignable to
－
conclusion and as such ν(O—H) does not appear in the
2 2 2 2 2 2
B2→ E, B2→ B1, B2→ A1, of square pyramidal ge- spectrum. A strong non-ligand band observed at 940

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FULL PAPER
cm 1 indicates the presence of V＝O. The new bands in
－
the far IR region are attributed to ν(M—N), ν(M—O).
Electronic spectrum shows three bands assignable to d-d
transitions of square pyramidal geometry. The bands
observed at 17543, 19600 cm 1 are assignable to 2B2→
－
2 2 2
E, B2→ B1 transitions and the band observed in the
region 27411—26315 cm 1 is due to 2B2→2A1 transi-
－
tion.
The EPR spectrum (Figure 3) clearly indicates poly-
crystalline nature of complex. The spectrum clearly
shows g║ and g┴ components usually seen in case of
oxovanadium complexes with axially symmetric g ten-
sor and hyperfine coupling (A) tensor. The g║, g┴, gav, A║,
A┴ and Aav values are evaluated as 1.9973, 2.0021,
1.9997, 104.40, 50.156 and 77.36 respectively. The
spectrum consists of at least thirteen lines in the place of
expected sixteen lines corresponding to hyperfine lines
of the A║ component and A┴ component. The central
region with intense signals corresponds to A component.
It is interesting to note that parallel and perpendicular
components of g do not differ as widely as expected for
oxovanadium(IV) ion[38] with octahedral environment
which obviously supports square pyramidal geometry.
The Δg (0.005) is at least 10 orders less than the Δg ex-
pected (0.03—0.09) for oxovanadium(IV) complexes
with fixed orientations. Since the Δg is unusually low
and giso (1.999) is closer to the free electron g value, the
complex must be having the unpaired electron loosely
bound to the metal ion.
Figure 3 EPR spectrum of [VO(HAHQO)2].
Characterization of [(VO)2(DHAHQO)2SO4]
The downward shifts in ν(C＝N)(ring), ν(C＝N)(exo)
and upward shifts in ν(C—Ο), ν(N—N) in IR spectrum
indicate binding of the ligand through an ONN sequence
involving phenolic oxygen and azomethine nitrogens.
No band is observed at 3000 cm 1, which is present in
－
the ligand, suggesting the deprotonation and coordina-
tion through phenolic oxygen. The stretching frequen-
cies of NH (ring and side chain), lactone carbonyl, lac-
tam carbonyl and ring C—O—C remain unchanged,
suggesting that non involvement of nitrogens of NH
(ring and side chain), oxygens of lactone carbonyl and
938 www.cjc.wiley-vch.de © 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Lakshmi, Satyanarayana & Reddy
lactam carbonyl in bonding. A medium intensity
non-ligand band observed at 910 cm 1 is assigned to
－
ν(V＝O). The three non-ligand bands appearing in the
region 1100—1140, 1030 and 600 cm 1 can be attrib-
－
uted to bidentate sulphate bridge. The new bands in the
far IR region are attributed to ν(M—N), ν(M—O).[39]
Electronic spectrum shows three bands at 17543, 20000
and 22727 cm 1, which are assignable to 2B2→2E,
－
2
B2→ B1 and B2→2A1 transitions of square pyramidal
2 2
geometry.
Characterization of [VO(NBHQO)2SO4]
The ν(C＝N) (free) has undergone a downward shift
by 20 cm 1, merging with the νC＝N (ring), concluding
－
that the nitrogen of azomethine (free) is participating in
M—L bonding. An upward shift of νNO2 (sym) by 20
cm 1 and a downward shift of νNO2 (asym) by 20 cm 1
－ －
indicate the binding of —NO2 group through its oxygen
atom.[40] The absence of sharp peak at 600 cm 1, corre-
－
sponding to the NO2 wagging mode of the ligand, fur-
ther confirms the coordination of one of the oxygens of
—NO2, which is characteristic of unidentate oxygen
bonded nitrite mode. The stretching frequencies con-
cerned with NH (ring and side chain) and lactam car-
bonyl remain unchanged, suggesting non involvement
of nitrogens of NH (ring and side chain), oxygen of lac-
tam carbonyl in bonding. A strong non-ligand band ob-
served at 920 cm 1 indicates the presence of V＝O. An
－
additional series of bands appeared at 1120, 1030, 640
cm 1, indicating the coordination of sulphate group in
－
unidentate manner[34] through oxygen atom. The other
new bands in the far IR region (Figure 4) are attributed
to ν(M—N), ν(M—O). Electronic spectrum shows three
bands at 11627, 16666 and 20000 cm 1, which are as-
－
signable to B2→ E, B2→ B1 and B2→2A1 transitions
2 2 2 2 2
respectively, indicating the complexes to be in distorted
octahedral environment.[41]
Figure 4 FT-IR spectrum of [VO(NBHQO)2SO4].
Antimicrobial activity
The results of preliminary screening tests are listed
in Table 3. These observations show that the majority of
the compounds are more active than the ligand. In some
Chin. J. Chem. 2012, 30, 935—940
Synthesis, Characterization and Antimicrobial Activity of Oxovanadium(IV) Complexes

cases, ligand and its complexes have similar activity acted as a monobasic bidentate ON donor through the
against bacteria. The observed increase in antimicrobial phenolic oxygen, azomethine (free) nitrogen and the
activity finds support from the literature[42-45] because ligand NBHQO acted as neutral bidentate ON donor
probably following factors can be operative. Such in- through oxygen of the nitro group and azomethine (free)
creased activity of the metal chelates can be explained nitrogen. On the basis of analytical, thermal, conductiv-
on the basis of Overtone's concept[42] and Tweedy's ity, magnetic and spectral data, square pyramidal ge-
chelation theory.[43] The lipid membrane that surrounds ometries have been proposed for all the complexes ex-
the cell favors the passage of only lipid soluble materi- cept for the complex of NBHQO to which distorted oc-
als due to which lipophilicity is an important factor tahedral geometry is assigned (Figures 5, 6, 7 and 8).
which controls the antimicrobial activity. On chelation,
the polarity of the metal ion will be reduced to a greater
extent due to the overlap of the ligand orbitals and par-
tial sharing of the positive charge of the metal ion with
the donor groups. Further, it increases the delocalization
of π-electrons over the whole chelate ring and hence N NH
enhances the liposolubility of the complexes. This in- O
creased liposolubility enhances the penetration of the HN
CH3
O N
complexes into the lipid membrane; the hydrocarbon V
tail functions as a lipophilic group to drive the com- N O O
H3C
pound through the semi permeable membrane of the cell; O
NH
and blocks the metal binding sites in the enzymes of
HN N
microorganisms.

Table 3 Antibacterial activity of ligands and complexes

Compound Antibacterial activity
zone of inhibition (mm)
Figure 6 Structure of [VO(HAHQO)2].
S. aureus (mg/L) E. coli (mg/L)
100 10 1 100 10 1
O O CH3
HSHQO 13 10 4 12 9 5
H3C
[(VO)2(SHQO)2SO4] 18 13 10 11 8 —
HHAHQO 11 8 3 — — — N O NH
HN O
V O N
[VO(HAHQO)2] O O S O O
16 11 9 — — — N O O V
NH
HN O N
HDHAHQO 19 13 11 12 9 2
CH3
[(VO)2(DHAHQO)2SO4] 19 13 11 3 2 —
H3C O
NBHQO 11 6 3 — — —
[VO(NBHQO)2SO4] 15 10 8 — — — Figure 7 Structure of (VO)2(DHAHQO)2SO4.
DMSO — — — — — —

N O NH HN N
HN O
V O N
O O S O O O NH
N O O V
NH N
HN O N O O O
N
N V
O O N
O
O3S HN O

Figure 5 Structure of [(VO)2(SHQO)2SO4]. N NH

Conclusions
The ligands HSHQO, HDHAHQO behaved as
monobasic tridentate ONN donors through phenolic
oxygen, azomethine nitrogens. The ligand HAHQO Figure 8 Structure of [VO(NBHQO)2SO4].

Chin. J. Chem. 2012, 30, 935—940 © 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.cjc.wiley-vch.de 939
FULL PAPER
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