Preparation, characterization, and antimicrobial activities of some mixed-ligand complexes of Mn(II), Co(II), Ni(II), Cu(II), and Cd(II) with monobasic bidentate (ON) Schiff base and neutral bidentate (NN) ligands

Article abstract of DOI:10.1081/SIM-120028308

Complexes of Mn(II), Co(II), Ni(II), Cu(II), and Cd(II) with 3,5-dibromosalicylidene-p-anisidene (HSB) and 2,2′-bipyridylamine (bipyamine) or bis(benzylidene)ethylenediamine (benen) or bis(acetophenone) ethylenediamine (acphen) have been prepared. They we

Full text of DOI:10.1081/SIM-120028308

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Preparation, Characterization, and Antimicrobial
Activities of Some Mixed‐Ligand Complexes of
Mn(II), Co(II), Ni(II), Cu(II), and Cd(II) with Monobasic
Bidentate (ON) Schiff Base and Neutral Bidentate
(NN) Ligands
Prakash P. Dholakiya a & M. N. Patel a
a Department of Chemistry , Sardar Patel University , Vallabh Vidyanagar, 388 120,
Gujarat, India
Published online: 16 Nov 2010.
To cite this article: Prakash P. Dholakiya & M. N. Patel (2004) Preparation, Characterization, and Antimicrobial Activities
of Some Mixed‐Ligand Complexes of Mn(II), Co(II), Ni(II), Cu(II), and Cd(II) with Monobasic Bidentate (ON) Schiff Base and
Neutral Bidentate (NN) Ligands, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 34:2, 383-395, DOI:
10.1081/SIM-120028308
To link to this article: http://dx.doi.org/10.1081/SIM-120028308
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SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY
Vol. 34, No. 2, pp. 383–395, 2004
Preparation, Characterization, and
Antimicrobial Activities of Some
Mixed-Ligand Complexes of Mn(II),
Co(II), Ni(II), Cu(II), and Cd(II)
with Monobasic Bidentate
(ON) Schiff Base and Neutral
Bidentate (NN) Ligands
*
Prakash P. Dholakiya and M. N. Patel
Department of Chemistry, Sardar Patel University,
Gujarat, India
ABSTRACT
Complexes of Mn(II), Co(II), Ni(II), Cu(II), and Cd(II) with 3,5-
dibromosalicylidene-p-anisidene (HSB) and 2,20-bipyridylamine (bipy-
amine) or bis(benzylidene)ethylenediamine (benen) or bis(acetophenone)
ethylenediamine (acphen) have been prepared. They were characterized
by elemental analyses, magnetic measurements, electronic and infrared
spectra. All the ligands, metal salts, and their complexes were screened for
*
Correspondence: M. N. Patel, Department of Chemistry, Sardar Patel University,
Vallabh Vidyanagar, 388 120, Gujarat, India; E-mail: jeenenpatel@yahoo.co.in.
383
DOI: 10.1081/SIM-120028308
0094-5714 (Print); 1532-2440 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

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Dholakiya and Patel
their antimicrobial activities against bacteria, yeast, and fungi and the
results are discussed.
Key Words: Ligands; Metal salts; Schiff bases; Antimicrobial activities.
INTRODUCTION
In order to emulate the biological activity of proteins and enzymes,[1]
various complexes containing Schiff bases have been prepared.[2] A lot of
work on the synthesis and biological activity of Schiff base metal complexes
has been done. These investigations show that these compounds are active
against bacteria, viruses, and cancers. In continuation of earlier work[3,4] the
present study describes the synthesis and characterization of the 3,5-
dibromosalicylidene-p-anisidene complexes of Mn(II), Co(II), Ni(II), Cu(II),
and Cd(II) with the HSB and their ligand replacement reactions with the
bidentate nitrogen donor ligands dipy-amine, benen, or acphen (Fig. 1). The
compounds were evaluated for their antimicrobial activities.
Figure 1. Structures of the ligands.

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385
Analytical Procedure
Elemental analyses for carbon, hydrogen, and nitrogen were carried out on
a model 240 Perkin–Elmer elemental analyzer. Metal contents were determined
by EDTA titration. The infrared spectra were measured on a Nicolet 400 D FT-
IR spectrophotometer in KBr pellets. The electronic spectra of the complexes
were recorded on a Beckman DK-2A spectrophotometer using MgO as the
reference. The melting points of the ligands and complexes were recorded in
open capillaries in a capillary melting point apparatus (Tempo Instruments Co;
Mumbai). The magnetic moments have been obtained by a vibrating sample
magnetometer (model 7304 LakeShore 735 Controller, 450 Gaussmeter).
EXPERIMENTAL
Materials
All chemicals used in the synthesis were of A. R. grade. 2,20-Bipyridyamine
was obtained from Lancaster (UK). Stock solutions of Mn(II), Co(II), Ni(II),
Cu(II), and Cd(II) chlorides were prepared and standardized by complexometric
titration.[5] Conductivity water was used in the synthesis of the complexes.
Preparation of the Schiff Bases
Bis(benzylidene)ethylenediamine (benen) was synthesized by a published
procedure.[6] The preparation of 3,5-dibromosalicylidene-p-anisidine was
carried out by refluxing a solution of 10 mmol of p-anisidine (1.23 g) in
100 mL ethanol with a solution of 10 mmol of 3,5-dibromosalicylaldehyde
(2.79 g) in 100 mL ethanol for 2–3 hr, and then allowing the reaction
mixture to cool to room temperature overnight. The yellow crystals formed
were collected, dried in air, and recrystallized from ethanol, yield: 3.01 g
(75.0%), melting point: 101 8C. anal. calcd for C13H9Br2N1O1 (355): C,
43.54%; H, 3.06%; N, 3.62%. Found: C, 43.50%; H, 3.02%; N, 3.60%.
The preparation of bis(acetophenone)ethylenediamine was carried out by
refluxing a solution of 10 mmol of acetophenone (1.20 g) in 100 mL ethanol
with a solution of 10 mmol of ethylenediamine (0.60 g) in 100 mL ethanol for
2–3 hr. The reaction mixture then was allowed to cool to room tempera-
ture overnight. The yellow microcrystals were collected, dried in air, and
recrystallized from ethanol, yield: 2.26 g (75.0%), melting point: 260 8C, anal.
calcd. for C18H20N2 (264): C, 81.81%; H, 7.57%; N, 10.60%. Found: C,
81.79%; H, 7.60%; N, 10.54%.

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Preparation of the Complexes
The bis(3,5-dibromosalicylidene-p-anisidine)diaquaM(II) complexes
[M ¼ Mn(II), Co(II), Ni(II), Cu(II), and Cd(II)] were synthesized by a
published procedure.[7] The preparation of mixed-ligand complexes of
bis(3,5-dibromosalicylidene-p-anisidine)acphenNi(II) or bis(3,5-dibromosali-
cylidene-p-anisidine)benenNi(II) was carried out by refluxing a solution of
2 mmol of bis(3,5-dibromosalicylidene-p-anisidine)diaquaNi(II) (0.37 g) in
100 mL dimethylformamide with a solution of 2 mmol of 2,20-bipyridylamine
(0.34 g) or bis-(benzylidene)ethylenediamine (0.47 g) or bis(acetophenone)
ethylenediamine (0.26 g) for an hour. The solution was then concentrated to
15 mL by evaporation, scratched, and cooled in a refrigerator overnight. The
obtained crystals were collected and recrystallized from chloroform and,
finally, dried in air. The complexes of Mn(II), Co(II), Cu(II), and Cd(II) were
prepared similarly.
RESULTS AND DISCUSSION
The percentage yields, colors, melting points, analytical and magnetic
moment data of the complexes are compiled in Table 1.
The compounds in this work were synthesized following the general
procedures outline in the following equations.
H2O
MCI2 ꢀ nH2O þ 2HSBꢁ![M(SB)2(H2O)2] þ 2HCl þ (n ꢁ 2)H2O
[M(SB) (H2O) ] þ bipy-amineꢁEtO!H, Reflux[M(SB) bipy-amine]þ2H2O
2
2
2
1 hr
EtOH, Reflux
[M(SB)2(H2O)2] þ benenꢁ![M(SB)2benen] þ 2H2O
1 hr
EtOH, Reflux
[M(SB)2(H2O)2] þ acphenꢁ![M(SB)2acphen] þ 2H2O
1 hr
The magnetic moment values of the Cu(II) complexes are 1.74, 1.79, and
1.71 B.M. and thus very close to the spin-only value (1.73 B.M.) expected for
one unpaired electron which is consistent with an octahedral geometry.[8] The
magnetic moment values of the Ni(II) complexes are 2.74, 2.98, and 2.74 B.M.
and are indicating that these complexes are also octahedral.[9] The magnetic
moment values of the Co(II) complexes are 4.00, 4.30, and 4.05 B.M. and are
in good agreement with a high-spin octahedral geometry.[10] The magnetic
moment values of the Mn(II) complexes are 6.00, 6.08, and 6.00 B.M.,
respectively, but are within the limits of spin-free values for five unpaired

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387
m

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Dholakiya and Patel
m

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Mixed-Ligand Complexes
389
electrons, indicating that the complexes are high-spin six-coordinated.[11] The
magnetic moment determinations show that the Cd(II) complexes are
diamagnetic and presumably octahedral.
The electronic spectra provide the most detailed information about the
electronic structure. The electronic spectra of the metal chelates have been
studied in the solid state between 350 and 1700nm. The electronic spectra of the
nickel(II) complexes exhibit three bands at ꢀ11,000, ꢀ19,000 and ꢀ 23,000
cm21, which may be due to the transitions[12] A2g(F) ! T2g(F) (v1),
3
3
3
3
3
3A2g(F) ! T1g(F) (v2), and A2g(F) ! T1g (P) (v3), respectively. The three
bands for the cobalt(II) complexes have been assigned to 4T1g(F) ! T2g (v1),
4
4
4
4
4T1g(F) ! A2g (v2), and T1g(F) ! T1g(P) (v3) at ꢀ9100, ꢀ18,000, and
ꢀ19,500cm21, respectively.[13] The electronic spectra of the copper(II)
complexes exhibit one band at ꢀ15,000cm21, which may be attributed to the
2
2
transition Eg ! T2g(F). These observations suggest an octahedral geometry
for these complexes.[14] The electronic spectra of the manganese(II) com-
plexes exhibit three weak absorption bands at ꢀ15,000, ꢀ19,000, and
ꢀ25,000cm21, which have been assigned to the transitions A1g ! T1g (4G)
6
4
(v1), 6A1g ! T2g (4G) (v2), and 6A1g ! A1g, 4Eg(4G) (v3), respectively, in an
octahedral field of Mn(II) ion.[15] The value of Dq, B, b, b0, and ratio v2/v1 for
the cobalt(II) and nickel(II) complexes are presented in Table 2.
4
4
The characteristic vibrational frequencies have been identified by
comparing the spectra of the complexes with those of their percursors and
literature values of absorption frequencies of similar compounds.[16] The Schiff
base (HSB) exhibits a medium-intense band at ꢀ2700cm21 due to
intramolecularly hydrogen bonded v(OH).[17] The absence of this band in the
complexes indicates the deprotonation of the phenolic groups and coordination
of the oxygen atoms to the metal ion. In the free ligand (HSB) a strong band
at 1525–1540cm21 due to v(C–O) (phenolic) shifts to higher energy by
5–10cm21 in the complexes indicating the coordination of the phenolic oxygen
atom to the metal ion. This shifts to higher energy as expected due to the
maintenance of ring currents arising from the electron delocalization in the
chelate ring. The Schiff base (HSB) shows the C55N stretching band at
1630cm21. This band shifts to lower energy by 10–15cm21 in the complexes
indicating coordination through the azomethine nitrogen.[17] The v(C55N)
frequency of 2,20-bipyridylamine occurs at 1585cm21. This band shifts to
higher energy by 35–45cm21 in the mixed-ligand complexes indicating the
bidentate (NN, pyridyl nitrogens) coordination of this heterocyclic ligand.[18]
The Schiff bases benen and acphen show the C55N stretching band at
ꢀ1640cm21. This band shifts to lower energy by 20–30cm21 in the mixed-
ligand complexes indicating coordination through the azomethine nitrogen.
The frequencies in the range 450–460 and 410–420 cm21 are attributed to
v(M–N)[19] and v(M–O),[20] respectively.

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Dholakiya and Patel
b

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391
Figure 2. Suggested structure of the complexes [M(SB)2bipy-amine].
The suggested structures of the complexes are shown in Figs. 2 and 3.
Antimicrobial Activity
The antimicrobial activity of the ligands, metal salts, and the
corresponding complexes were assayed against Salmonella typhi (bacteria)
and Saccharomyces cerevisiae (yeast) using the “Agar Diffusion Method.”[21]
Figure 3. Suggested structure of the complexes [M(SB)2benen]; (X ¼ H) or
[M(SB)2acphen]; (X ¼ CH3).

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Dholakiya and Patel
The antifungal activity of the complexes were assayed against Fusarium
oxysporum and Lasiodiplodia theobromae (fungi) using the “Potato Dextrose
Agar Method.”[22] All the compounds have significant antibacterial activity at
5 ꢂ 1024 g mL21 against bacteria, yeast, and fungi. The results were
compared against dimethyl formamide as the control and are expressed as
percentage vs. control. The percentage inhibition of various compounds are
recorded in Table 3. The data represent the values of five replicates. From the
data it is observed that the complexes show higher activity against bacteria,
yeast, and fungi as compared to control, ligands, and metal salts. The results
Table 3. Antimicrobial activities of the complexes.a
% Inhibition
Fungi
Bacteria Yeast
(S. typhi) (S. cerevisiae)
Lasiodiplodia Fusarium
theobromae oxysporum
Compound
.
MnCl2 4H2O
21.11
16.66
11.11
22.22
16.66
33.33
11.11
26.00
37.00
50.00
50.00
55.00
55.00
55.00
50.00
66.66
61.11
55.00
50.00
66.66
50.00
55.00
66.66
44.48
21.05
10.52
05.26
15.78
05.26
31.57
05.26
10.50
05.00
42.10
47.36
52.63
42.10
52.63
47.36
47.36
52.63
42.10
42.00
50.00
47.36
36.84
47.36
42.10
13.30
06.60
13.30
20.00
06.60
20.00
06.60
26.00
20.00
60.00
46.60
33.30
60.00
40.00
46.60
40.00
33.30
33.30
60.00
46.60
33.30
53.60
60.60
40.00
15.30
15.30
13.10
07.70
13.00
27.00
07.70
23.00
37.00
53.00
53.00
46.00
46.00
51.03
61.30
61.00
53.00
46.00
53.00
61.30
61.00
53.80
46.00
61.30
.
CoCl2 6H2O
.
NiCl2 6H2O
.
CuCl2 2H2O
.
CdCl2 H2O
HSB
Bipy-amine
acphen
benen
[Mn(SB)2bipy-amine]
[Co(SB)2bipy-amine]
[Ni(SB)2bipy-amine]
[Cu(SB)2bipy-amine]
[Cd(SB)2bipy-amine]
[Mn(SB)2benen]
[Co(SB)2benen]
[Ni(SB)2benen]
[Cu(SB)2benen]
[Cd(SB)2benen]
[Mn(SB)2acphen]
[Co(SB)2acphen]
[Ni(SB)2acphen]
[Cu(SB)2acphen]
[Cd(SB)2acphen]
aHSB ¼ 3,5-Dibromosalicylidene-p-anisidine.

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393
suggest that the change in the structure due to coordination in the mixed-
ligand complexes decreases the growth of microorganisms. Hence, com-
plexation increases the antimicrobial activity. The complexes show greater
activity against S. typhi (bacteria) than S. cereuisae (yeast). The patterns of
activity are complex and no clear trend can be ascertained.
ACKNOWLEDGMENTS
We wish to thank Prof. R. M. Patel, Head, Department of Chemistry and
Prof. I. L. Kothari, Head, Department of Bio-Sciences, Sardar Patel
University, Vallabh Vidyanagar, India, for providing the necessary laboratory
facilities.
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Accepted October 23, 2003
Referee I: K. Moedritzer
Referee II: E. J. Valente

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