EUROPEAN ACADEMIC RESEARCH

Vol. II, Issue 4/ July 2014

ISSN 2286-4822
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Synthesis, characterization and antimicrobial

activity of transition metal complexes with Schiff
base derived from 1, 2-diphenylethane-1, 2-dione
with o-phenylenediamine and benzophenone
PARVEEZ GULL
Research Scholar
Inorganic Research Lab., Department of Chemistry
Jamia Millia Islamia, New Delhi
India

ATHAR ADIL HASHMI

Associate Professor
Inorganic Research Lab., Department of Chemistry
Jamia Millia Islamia, New Delhi
India
[email protected]

Abstract:
Novel Schiff base ligand (L1) was derived from 1,2diphenylethane-1,2-dione with O-phenylenediamine and benzophenone
and their metal complexes with the transition metals Co (II), Cu (II)
and Zn (II) have been prepared by using a molar ratio of ligand: metal
as 1:1. These metal complexes were characterised by the various
sophisticated techniques like FTIR, UV-Visible, NMR, and Mass
spectrophotometry. These characterizations have concluded that the
Schiff base ligand formed acts as a tetradentate ligand and
coordinates with the transition metals involved through the four
azomethine nitrogen atoms. The structure and bonding nature of all
the compounds showed that all complexes possessed an octahedral
geometry except the Cu (II) complexes which showed a distorted
octahedral geometry. Mass spectrum explains the successive
degradation of the molecular species in solution. All the synthesized
compounds were studied for their in vitro antibacterial, and
antifungal activities, against Staphylococcus aureus, Bacillus subtilis,
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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

Escherichia coli, Klebsiella pneumoniae and Salmonella typhi

bacterial strains and against five fungal strains Aspergillus niger,
Fusarium solani, Curvularia lunata, Rhizoctonia bataicola and
Candida albicans by using agar-well diffusion method. It has been
shown that all the synthesized compounds showed moderate to
significant antibacterial activity against one or more bacterial strains.
Key words: Synthesis, characterization, antimicrobial activity,
transition metal complexes

Introduction
Coordination Chemistry gave the beautiful chance to Schiff
bases and their metal complexes to emerge as a diverse field of
chemistry. Now-a-days these metal complexes play an
important role in the development and progress of coordination
chemistry [13]. The literature clearly shows that the study of
this diverse ligand system is linked with many of the key
advances made in inorganic chemistry [4, 5]. Although the
magnetic, spectroscopic and catalytic properties of these Schiffbase complexes are well documented [6, 7]. Presently, the
coordination chemistry of structurally modified bio-ligands and
the transition metal complexes with potential biological activity
are the focus of extensive investigations in front of inorganic
chemists. Schiff base ligands have received special attention
because of their mixed softhard donor character, versatile
coordination behaviour [8]. Structural factors such as ligand
rigidity, the types of donor atoms and their disposition have
shown to play significant roles in determining the binding
features of these ligands toward metal cations. The chelating
ability of Schiff bases gives them the place in the coordination
chemistry and are used as chelating agents [9-11], in catalysis,
anti-oxidative activity, medicine as antibiotics, antiinflammatory agents and in industry for anti-corrosion
properties [12-15]. A considerable number of Schiff-base
complexes have potential biological interest and are used as
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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

more or less successful models of biological compounds [16]. The

research field dealing with Schiff base metal complexes is very
broad due in part to their potential interest for a number of
interdisciplinary areas that include bioinorganic chemistry,
catalysis, and magneto chemistry [1721]. The preparation of
Schiff bases containing >C=N groups with potential ligating
ability has drawn a lot of attention because of their use as
chelating agents, analytical reagents, metal indicators in
complexometric titrations and calorimetric reagents, in addition
to biochemical research [22]. The behaviour of the >C=N bond
is strongly dependent on the structure of the amine moiety,
which in turn controls the efficiency of the conjugation and may
incorporate structural elements able to modulate the steric
crowding around the coordination [23]. In view of above
applications, in this present paper we report synthesis and
characterization of Co (II), Cu (II) and Zn (II) complexes derived
from 1,2-diphenylethane-1,2-dione, o-phenylenediamine and
benzophenone. Besides the characterization of complexes by
standard technique like IR, NMR, elemental analyses, magnetic
susceptibility and conductance measurements, the biological
activities of the synthesized complexes have been examined
against some antimicrobial strains for evaluation of
antibacterial and antifungal activities of the synthesized
chemical compounds. The results obtained were compared with
standard drugs: Fluconazole and Kanamycin.
Experimental protocols
Reagents and instruments
Laboratory reagent grade O-phenylenediamine and 1, 2diphenylethane-1,2-dione were obtained from E Merck
(Germany), benzophenone from Aldrich. The analytical grade
metallic salts CoCl26H2O, CuCl2.6H2O and ZnCl2.4H2O were
obtained from E Merck (Germany). Absolute alcohol was
obtained from E Merck (Germany) and methanol from Sd-Fine
Chemicals (India).Hydrochloric acid was obtained from E Merck
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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

(Germany). Double distilled water was used in all experimental

work. All chemicals were used without further purification.1H
NMR spectra were recorded with a Bruker Advance II
spectrometer operating at 400 MHz using CDCl3 as internal
standard for ligand L1 and DMSO for its metal complexes ML.
FTIR spectra were recorded in the range of 4000 - 400 cm1 on
Perkin-Elmer FTIR spectrometer, using KBr pellets. The
elemental analysis (C, H and N) of the complexes were
performed using Elementar vario EL III (Germany) model. The
molar conductance at 103M dilution was measured by ElicoConductometer Bridge. The UVvisible spectra were recorded
in methanol on Beckman DU-64 spectrophotometer with quartz
cells of 1 cm path length. Antimicrobial studies have been done
at Center of Research for Development, University of Kashmir.
Preparation of Schiffs Base.
Preparation of N1-(diphenylmethylene) benzene-1, 2diamine (L)
O-phenylenediamine (4.55g, 0.025mol) in ethanol solution
(30ml) was added to magnetically stirred ethanolic solution (30
ml) of benzophenone (2.70g, 0.025 mol) and mixture was
refluxed for 6 hours through monitoring by TLC. After
completion of the reaction, the resultant mixture was cooled to
room temperature, filtered and reduced nearly half of its
volume by rotary evaporator. It was then allowed to stay at
room temperature for 3 h which resulted in the solid product. It
was filtered, washed with methanol and recrystallized with a
mixture of ethanol: methanol (1:1). The crystalline product
obtained was dried over fused calcium chloride in desiccators.
L: Yield: 68%. Anal. Calc. for C19H16N2: C, 83.79; H, 5.92;
N, 10.29 (%); Found: C, 79.5; H, 4.5; N, 10.1 (%). IR (KBr pellet,
cm-1): 1632 (C=N);, 3204, (NH str;). 1H NMR (d):
(aromatic) 7.28.2 (m); (aromaticCNH),4.0 (s).

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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

Preparation of (E)-N1-(diphenylmethylene)-N2-((E)-2-(2
(diphenylmethyleneamino)
phenylimino)-1,
2diphenylethylidene) benzene-1, 2-diamine (L1)
A hot ethanolic solution (25 mL) of N1-(diphenylmethylene)
benzene-1, 2-diamine (L) (5.25 g, 0.050 mol), and a hot
ethanolic solution (25 mL) of 1, 2-diphenylethane-1,2-dione
(2.62 g, 0.025 mol) were mixed slowly with constant stirring.
The mixture was refluxed at 75 C for 810 h in presence of few
drops of concentrated HCl. On cooling, a crystalline product
was formed, which was filtered, washed with cold ethanol, and
dried under vacuum over P4O10 (Scheme 1).
L1. Yield: 63%. Anal. Calc. for C52H38N4: C, 86.88; H,
5.33; N, 7.79; Found: C, 88.3; H, 5.28; N, 7.60 (%). IR (KBr
pellet, cm-1) 1638 (C=N); 1525 (HC=C). 1H NMR (, ppm):
(aromatic) 7.08.0 (m). MS m/z (%): 719 [M+1]+. max (cm-1) in
EtOH, 26,666-28,237 cm-1.

O
NH2

pH 3-4
N

Reflux 6 hrs

NH2
o-phenylene diamine

NH2

Benzophenone

O
N

N
N

Reflux 6 hrs

NH2

L1

Scheme 1: Synthesis of the ligand

Preparation of LigandMetal Complexes.

Complexation of ligand L1 was carried out separately with the
metal salts CoCl2.6H2O, CuCl2.4H2O and ZnCl2 by refluxing
with continuous stirring (1:1 molar ratio) of ligand and metal
salts dissolved in ethanol for 3 h. The crystalline products thus
obtained were filtered, washed with aqueous methanolic
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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

solution and finally dried over fused calcium chloride in

desiccators. The color of the L1CoCl2 complex was Pink and
that of the L1CuCl2 complex was Green. A similar procedure
was followed for complexing ligand L1 separately with ZnCl2. In
this case refluxing with stirring was done for 34 h. and the
color of the complex was Pale brown.
[CoL1Cl2]. Yield: 60%. Anal. Calc. for C52H38N4CoCl2:
Co, 6.94; C, 73.59; H, 4.51; N, 6.60(%); Found: Co, 6.92; C,
73.58; H, 4.50; N, 6.59 (%). IR (KBr pellet, cm-1): 1608 (C=N);
1497 (HC=C); 1472, 1306, 423 (MN). MS m/z (%): 849
[M+1]+. M 10-3 (ohm-1 cm2 mol-1) = 5.5. UVVis (DMF, 103 M)
max (cm-1), 16,146 18,416
[CuL1Cl2]. Yield: 61%. Anal. Calc. for C52H38N4CuCl2:
Cu, 7.45; C, 73.19; H, 4.49; N, 6.57; Cl,8.31 Found: Cu, 7.44; C,
60.9; H, 4.6; N, 5.8 (%). IR (KBr pellet, cm-1): 1608 (C=N); 1507
(HC=C); 437 (MN). MS m/z (%): 853 [M+1]+. M 10-3 (ohm-1
cm2 mol-1) = 9.2. UVVis (DMF, 103 M) max (cm-1), 22,552 26,659 cm-1
[ZnL1Cl2]. Yield: 59%. Anal. Calc. for C52H38N4ZnCl2:
Zn, 7.65; C, 73.19; H, 4.49; N, 5.6; Found: Zn, 7.55; C, 72.9; H,
4.45; N, 5.5 (%). IR (KBr pellet, cm-1): 1612 (C=N); 1522
(HC=C); 441 (MN). MS m/z (%): 852 [M+1]+. M 10-3 (ohm-1
cm2mol-1) = 4.3. UVVis (DMF, 103 M) max (cm-1), 28,46031,950cm-1

M
N

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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

Fig. 1. Proposed structure of synthesized complexes where M = Co

(II), Cu (II), and Zn (II) and Where X = Cl-

Evaluation of antimicrobial activity

Qualitative determination of antimicrobial activity was done
using the disc diffusion method. The biological activities of
synthesized Schiff base and its metal complexes were studied
for their antibacterial and antifungal activities in DMF solvent
against bacterial and fungi species. Suspensions in sterile
peptone water from 24 h cultures of microorganisms were
adjusted to 0.5 McFarland. MullerHinton petri discs of 90 mm
were inoculated using these suspensions. Paper discs (6 mm in
diameter) containing 10 L of the substance to be tested were
placed in a circular pattern in each inoculated plate. DMF
impregnated discs were used as negative controls. Toxicity tests
of the solvent, DMF, showed that the concentration used in
antibacterial activity assays did not interfere with the growth
of the microorganisms.
Determination of MIC
The in vitro antimicrobial activity was performed against Gram
positive bacteria: Staphylococcus aureus, Bacillus subtilis,
Escherichia coli, Klebsiella pneumoniae and Salmonella typhi
bacterial strains and against five fungal strains Aspergillus
niger, Fusarium solani, Curvularia lunata, Rhizoctonia
bataicola and Candida albicans. The standard and test samples
were dissolved in DMF to give a concentration of 100 g/mL.
The minimum inhibitory concentration (MIC) was determined
by broth micro dilution method [24]. Dilutions of test and
standard compounds were prepared in nutrient broth (bacteria)
or Sabouraud dextrose broth (fungi) [25]. The samples were
incubated at 37C for 24 h (bacteria) and at 25C for 48 h
(fungi), respectively, and the results were recorded in terms of
MIC (the lowest concentration of test substance which inhibited
the growth of microorganisms).
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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

Results and discussion

The spectral and analytical data show the formula of the Co
(II), Cu(II) and Zn(II) complexes as [CoL1Cl2] , [CuL1Cl2 and
[ZnL1Cl2]. All the Co(II), Cu(II) and Zn(II) complexes are
colored, stable in air and non-hygroscopic solids. They are
sparingly soluble in all organic solvents. The elemental
analyses show that the Co(II), Cu(II) and Zn(II) complexes have
a 1:1 stoichiometry of the type M:L. The molar conductance
values at 10-3 M concentration are too low to account for any
dissociation of the complexes in DMF. Hence, the Co(II), Cu(II)
and Zn(II) complexes may be regarded as non-electrolytes. The
spectroscopic and magnetic studies conclude an octahedral
geometry for the Co(II) and distorted octahedral for Cu(II)
complexes and a six coordinated octahedral geometry for the
Zn(II) complexes.
Infrared spectra
The coordination mode and sites of the ligand to the metal ions
were investigated by comparing the infrared spectra of the free
ligand with its metal complexes. The band found in the region
of 16381631 cm-1 is the characteristic of the (C=N) stretching
mode [2628] indicates the formation of the Schiff base
compound containing (C=N) group in the compound L. The
presence of the bands 1625 cm-1 in the compound L1 indicates
the formation of azomethine group .The shifting of this band to
lower frequency by ca. 30 cm-1 on complexation compared to free
ligands indicates the involvement of the azomethine nitrogen in
chelation with the metal ion, the coordination of the nitrogen to
the metal ion would be expected to reduce the electron density
of the azomethine link and thus causes a shift in the (C=N)
group [29]. Coupled with this, the absence of a band around
16801710 cm-1 [30], characteristic of (C=O) in 1,2diphenylethane-1,2-dione, suggests that the condensation of the
keto groups is complete. Conclusive evidence of the bonding is
also shown by the observation that new bands appear in the
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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

Transmittance(%)

spectra of all metal complexes in the low frequency regions at

420447 and 360389 cm-1 characteristic for MN and MCl
vibrations, respectively, which are not observed in the spectra
of free ligands.

2500

2000

1500

1000

-1

Wavelength(cm )

Fig. 2 FT-IR spectrum of L1

Molar conductivity
The complexes are found to be non-electrolytic nature in 10-3 M
DMF solution, implying the coordination of chloride anion to
the central metal ion. The lower conductance values (3.79.2 1cm-2mol-1) of the complexes support their non-electrolytic
nature. The elemental analysis results of the metal complexes
also agree with the calculated values, showing that the
complexes have 1:1 metal/ligand ratio.
Magnetic moments and electronic spectra
The geometry of the metal complexes has been deduced from
electronic spectra and magnetic data of the complexes. The
electronic spectra of the complexes were recorded in solution.
The free ligands exhibit two intense bands in 44,75440,546
and 28,261 26,139 cm-1 region due to * and n*
transitions [31], respectively. In all the metal complexes, the
absorption bands at 28,53934,161 cm-1 are due to * and
n* transitions that are observed in the spectra of the free
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ligand L1. These transitions are shifted to blue or red

frequencies due to the coordination of the ligand with metal
ions. The electronic spectra of Co(II) complexes show broad,
intensity bands in the visible region, around 16,146 17,416 cm1, which are assigned to the combination of 2B1g2A1g and
2B 2E transitions respectively. The electronic spectral data
1g
g
suggest a octahedral around the Co(II) ion. The observed
magnetic moment of the Co(II) complexes (1.811.87 B.M) at
room temperature indicates the non-coupled mononuclear
complexes of magnetically diluted d9 system with S = 1/2 spinstate. The electronic spectrum of the copper (II) complex shows
bathochromic shifts in the absorption frequencies azomethine
chromophore. The band structure observed between 26,666 28,237 cm-1 in free ligand spectrum appears to shift to 22,552 26,659 cm -1. This is a consequence of the involvement
azomethine functions in chelation. The electronic absorption
spectra of the diamagnetic Zn(II) complexes show the bands at
28,460-31,950cm-1 which are assigned to intra-ligand charge
transfer transitions.
NMR spectra of zinc complexes
In 1H NMR, the aromatic region is a set of multiplets in the
range of 7.08.2 ppm for all the ligands and their complexes.
There is no appreciable change in all other signals of the
complex. (Fig. 3a-3c)

Fig. 3a NMR of [CoL1Cl2].

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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

Fig. 3b NMR of [CuL1Cl2].

Fig.3c NMR of [ZnL1Cl2].

Thermogravimetric studies
The thermal behaviors of Co2+ complexes have been studied, as
a function of temperature. The thermal decomposition of [Co
(L1)Cl2] complexe took place in two step as indicated by DTG
peaks around 370C and 540C respectively corresponding to
the mass loss of organic moiety. Hence, finally the metal
complexes decompose gradually with the formation of metal
oxide above 540C.
Mass spectra
The ESI-mass spectra of synthesized ligands and their
complexes were recorded and the obtained molecular ion peaks
confirm the proposed formulae. The mass spectrum of L1 ligand
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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

shows M+1 peak at m/z 719 (86.4%) corresponding to

[C52H38N4] + ion. The mass spectrum of [CuL1Cl2] shows peaks
at m/z 753 with 63.9% abundances. The strongest peaks (base
beak) at m/z 719 represent the stable species C52H38N4. The m/z
of all the fragments of ligands and their complexes confirm the
stoichiometry of the complexes as [MLCl2]. The observed peaks
are in good agreement with their formulae as expressed from
micro analytical data. Thus, the mass spectral data reinforce
the conclusion drawn from the analytical and conductance
values.
Antimicrobial activity
The minimal inhibitory concentrations of tested schiff base
metal complexes against certain bacteria and fungi are shown
in Tables 1 and 2. The ligand (L1) and their metal complexes
were prepared and tested for their in vitro antimicrobial
activity against the five strains of bacteria (gram negative and
gram positive), and five strains of fungi. Few metal complexes
showed high in vitro antimicrobial activity. All the Co(II) and
Cu(II) metal complexes showed significant antibacterial and
antifungal activities compared to free ligands, But the activity
was lesser than the standard drugs. It is clearly depicted in
Figs.5a and 5b. Such increased activity of the complexes can be
explained on the basis of Overtones concept [33] and the
Tweedys Chelation theory [34].The nature of metal ion also
plays a decisive role in determining antimicrobial properties. In
the present study, the order of the antimicrobial activity of the
synthesized compounds (based on the metal atom present)
follows: Co > Cu > Zn > L1. The mode of action of the
compounds may involve the formation of a hydrogen bond
through the azomethine group with the active centres of cell
constituents, resulting in interferences with the normal cell
process [35, 36].

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Table 1 Minimum inhibitory concentration of the synthesized compounds

against growth of bacteria (g/mL).
Compound

Minimum inhibitory concentration (MIC) ( x 104 M)

Staphylococcus Bacillus
Escherichia Klebsiella
aureus
subtilis
coli
pneumoniae
9.1
9.5
10
9.7
5.5
5.1
4.9
5.5
6.1
6.5
6.1
6.8
7.2
7.8
7
7.3
1.5
2.5
1.2
2

L1
[CoL1Cl2]
[CuL1Cl2]
[ZnL1Cl2]
Kanamycina
a

Salmonella
typhi
9.2
5.3
6.5
7.5
2.2

Kanamycin is used as the standard.

Table 2 Minimum inhibitory concentration of the synthesized compounds

against the growth of fungi (g/mL).
Compound

Minimum inhibitory concentration (MIC) (x104 M )

Aspergillus Fusarium
Curvularia
Rhizoctonia
niger
solani
lunata
bataicola
8.2
8.5
8
8
6.5
6.2
6
6.8
5.9
5.8
6.2
6.3
8.5
8.9
8
8.3
1.3
1.6
1.1
1.4

L1
[CoL1Cl2]
[CuL1Cl2]
[ZnL1Cl2]
Fluconazolea

Candida
albicans
8.2
6.1
6.5
8.5
1.7

10
S.aureus
B. subtilis
E. coli
K. pneumoniae
S. typhi

MIC

0
L1

[CoL1Cl2]

[CuL1Cl2]

[ZnL1Cl2]

Kanamycina

Compound

Fig. 5a. Minimum inhibitory concentration of the synthesized

compounds against the growth of bacteria (g/mL).

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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

A. niger
F. solani
C. lunata
R. bataicola
C. albicans

MIC

0
L1

[CoL1Cl2]

[CuL1Cl2]

[ZnL1Cl2]

Fluconazolea

Compound

Fig.5b. Minimum inhibitory concentration

compounds against growth of fungi (g/mL).

of

the

synthesized

Conclusion
In this paper, few novel Schiff bases and their Co(II) ,Cu(II) and
Zn(II) complexes have been synthesized and characterized by
sophisticated techniques and analytical data. The IR, electronic
transition and g tensor data lead to the conclusion that the
central metal ion assumes a octahedral geometry. We have
evaluated in vitro the antibacterial and antifungal of newly
synthesized Schiff base ligands and their metal complexes. The
cobalt (II) complex of L1 has higher potency against Grampositive bacteria than Gram-negative bacteria.
Acknowledgments
The authors are grateful to the Head of Department of the Chemistry
for providing the necessary facilities. The authors are also thankful to
UGC, New Delhi, for providing financial assistance.

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activity of transition metal complexes with Schiff base derived from 1, 2diphenylethane-1, 2-dione with o-phenylenediamine and benzophenone

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