International Journal of Engineering and Science Invention (IJESI)

International Journal of Engineering Science Invention
ISSN (Online): 2319 – 6734, ISSN (Print): 2319 – 6726
www.ijesi.org Volume 2 Issue 6 ǁ June. 2013 ǁ PP.48-52
www.ijesi.org 48 | Page
Spectroscopic and Antimicrobial study of Co (II) and Cu (II)
Schiff base Metal Complexes
M.M. Jagadalea
, M.R.Asabeb
and V.P. Ubalea
*
a
Department of Chemistry, D.B.F. Dayanand College, Solapur, Maharashtra, 413002, India.
b
Department of Chemistry, Walchand College of Arts and Science, Solapur, Maharashtra, 413002, India.
ABSTRACT: Schiff base ligand N, N’ (2 hydroxybenzaldehyde) diamino diphenyl ether [HL] and its Co (II)
and Cu (II) metal complexes were synthesized. The ligand and metal complexes were characterized by UV-
visible, FTIR and 1
H NMR spectroscopy. The ligand [HL] was synthesized by condensation of 2-
hydroxybenzaldehyde and 4, 4’diaminodiphenyl ether. The ligand and metal (II) complexes were also screened
for their antimicrobial activity against microorganisms Staphylococcus aureus and Pseudomonas aeruginosa.
KEYWORDS: Transition metal complexes, 4, 4’diaminodiphenyl ether, Schiff base, and Antibacterial activity.
I. INTRODUCTION
Transition metal complexes with various donor groups have been used in organometallic chemistry [1].
A large number of Schiff base compounds have been synthesized and structurally characterized [2–6]. The
various classes of Schiff bases that can be prepared by condensation of different types of amines and carbonyl
compounds are very popular due to diverse chelating ability. Several transition metal complexes have been
screened for their medicinal properties [7–19].
The Schiff base complexes are important as medicine and show a variety of interesting biological
activities such as antibacterial and antifungal activity [20-21]. Transition metal complexes with various donor
groups have been used in organometallic chemistry. A large number of Schiff base compounds have been
synthesized and structurally characterized [22-23].
The various classes of Schiff bases that can be prepared by condensation of different types of amines
and carbonyl compounds are very popular due to diverse chelating ability. Several transition metal complexes
have been screened for their medicinal properties. The first row transition metals have attracted much attention
due to their biological importance [24].These factors prompted us to carry out a study on synthesis of Schiff
base and its complexes with Co (II) and Cu (II) metal ions.
In this paper we report the synthesis of new Schiff base ligand N, N’ (2 hydroxybenzaldehyde) diamino
diphenyl ether [HL] and its legation behavior with Co (II) and Cu (II) metals. The synthesized ligand and metal
complexes were characterized by elemental analysis, Uv-Visible, FTIR and 1
H NMR. They are also screened for
their biological activities against the microorganism Pseudomonas aeruginosa and Staphylococcus aureus.
II. MATERIALS AND METHODS
All reagents used were pure AR grade such as 2 hydroxybenzaldehyde, 4, 4’diaminodiphenyl ether,
Nickel chloride and Zinc chloride. The solvents used were ethanol and Dichloromethane. The synthesis of
Schiff base ligand and metal complexes is shown in Scheme 1.
The 2 hydroxybenzaldehyde (4.88 g, 0.2 mol) and 4, 4’diaminodiphenyl ether (4.0 g, 0.1mol) were
dissolved in ethanol (25 ml) separately in 2:1 molar ratio. The ethanolic solutions were mixed together. The
mixture was refluxed on oil bath for 3 hrs. On cooling, a crystalline complex was separated by filtration and the
crystals were washed with ethanol and anhydrous diethyl ether and dried over anhydrous CaCl2 [25-28].
A ligand (0.408g, 0.01 mol) [HL] was dissolved in (25ml) Dichloromethane and added to a metal salt
[cobalt chloride (0.474 g, 0.01 mol), and copper chloride (0.454 g, 0.01 mol)] ethanolic solution (25 ml). The
metal-ligand molar ratio was (2:1). The mixture was refluxed for 2 hrs. On cooling, a crystalline complex was
separated by filtration and the crystals were washed and dried.
III. RESULTS AND DISCUSSION
Analytical and physical data of the compounds studied is reported in Table 1. The ligand and the metal
(II) complexes are soluble in common polar solvents like Chloroform, Dichloromethane and Dimethyl
acetamide. The synthesized ligand and the metal complexes were characterized by spectral analysis. Biological
activity of the ligand and the metal complexes were also studied.

Synthesis, Spectral and Antimicrobial study of Cu (II)…
The electronic spectra are very useful in the evaluation of results obtained by other methods of
structural investigation. Information regarding the geometry of the complexes around the Co (II) and Cu (II)
ions was obtained from electronic spectral studies. The electronic spectra of ligand and their metal complexes
were recorded at room temperature using Dichloromethane as a solvent.
The electronic spectra of ligand show bands in the region of 234 nm and 278 nm but in the complexes
they are slightly shifted to higher frequencies. The band between 375 nm can be assigned to n π * of
transition of azomethine group. In the spectra of complexes the bands of azomethine chromophore n π*
transition are shifted to lower frequencies indicates that imine nitrogen is involved in the co-ordination of metal
ion. A very weak low intensity absorption band associated with d-d transition for Co (II) complexes at 465, 532
nm (typical octahedral transition) and for Cu (II) complexes at 470 nm (Charge transfer), 525nm
[3
A2g(F) 3
T1g(P)], 985 nm [ 3
A2g
3
T1g(F)] respectively supports the octahedral geometry of metal
complexes [29].
The IR spectral data of Schiff base [HL] and their metal complexes are presented in Table 2. The IR
spectra of complexes are compared with those of ligand in order to determine the coordination sites that may be
involved in chelation. A strong band observed at 1620 cm-1
in a ligand [HL] is a characteristic band of (HC=N)
azomethine group. The shifting of this band towards lower frequency region by 10 -15 cm-1
in complexes
indicates involvement of azomethine nitrogen in coordination with metal ion [30-32]. The assignment of the
proposed coordination sites is further supported by appearance of band at 521-544 cm-1
suggesting the
υ (M-N) bond. The presence of υ (M-O) stretching vibration at 740-750 cm-1
supports the involvement of
oxygen atom in complexation with metal ions. The ligand and metal complexes were characterized mainly using
the azomethine and –OH bands. In the complexes, the broad band in the range of 3357-3365 cm-1
is attributed
to the presence of water molecules. Therefore, from the IR spectra, it is concluded, that the ligand coordinated to
the metal ions via azomethine nitrogen and deprotonated oxygen atom from 2 hydroxybenzaldehyde.
The antibacterial activity of the Schiff bases and their metal complexes was tested on Staphylococcus
aureus, Pseudomonas aeruginosa. The method used for antibacterial activity was Agar Well-Diffusion method
[33]. The stock solution 1mg/ml was prepared and was used to prepare concentrations of 8, 6, 4 and 2 ug/l. The
bacteria and fungi were inoculated on the surface of Nutrient agar and Sabouraud’s agar, respectively. The
various concentrations of the compounds were inoculated in the wells prepared on the agar plates. The plates
were incubated at room temperature for 24h. In order to clarify the effect of Dimethylformamide on the
biological screening, separate studies were carried out with Dimethylformamide (DMF) and showed no activity
against any bacteria. The results are as summarized in the Table 3.
IV. CONCLUSION
The Co and Cu complexes have octahedral geometry. The Copper (C26H20N2O32Cu.4H2O) and the
Cobalt complexes (C26H20N2O32Co.4H2O) are moderately active against the Staphylococcus aureus. The highest
activity is observed for Copper complex.
REFERENCES
[1]. I.S. Patai, The Chemistry of the Hydrazo, Azo, Azoxy Groups, Part-1 Wiley, New York. (1975).
[2]. I.M. Awad, A.A. Aly, A.M. Abdel Alim, R.A. Abdel Aal, S.H. Ahmed, J. of Inorg. Biochem. 33 (1998) 77.
[3]. A.G. Makshumov, M.S. Ergashev, F.A. Normatov, Pharm. Chem. J.25 (1991) 1.
[4]. A.A. Jarahour, M. Motamedifar, K. Pakshir, N. Hadi, Z. Zarei, Molecules. 9 (2004) 815.
[5]. K.Y. Law. Chem. Rev. (1993) 449.
[6]. A. Kleeman, J. Engel, B. Kutscher. D. Reichert, Pharmaceuticals Substances, 3rd
Edn.Thieme, Stuttgart, 1999.
[7]. A.R. Sarkar, S. Mandal, Synth. React. Inorg. Met.-Org. Chem. 80(2008) 1477.
[8]. Offiong E Offiong, Spectrochimica Acta. 50 (1994) 2167.
[9]. MTH Tarafder, Ali M Akbar, Can. J. Chem. 56 (1978) 2000.
S.J. Swamy, A. Dharma Reddy, J. Indian Chem. Soc. 77 (2000) 336.
[10]. B.D. Sharma, J.C. Bailur, J. Am. Chem. Soc. 77 (1955) 5476.
[11]. F.P. Dwyer, M.S. Gill, E.C. Gyarfas, F. J. Lion, Am. Chem. Soc.79 (1957) 1269.
[12]. Salib Kar, S.M. Elsayed, A.M. Elshabiny, Synth. React. Inorg. Met.-Org.Chem. 21 (10) (1990) 1511.
[13]. B.A. Mahapatra, S.K. Kar, Orient. J.Chem. 10 (3) (1954) 259.
[14]. P.P. Hankare, P.H. Bhoite, P.S. Battse, K.M. Garadkar, A.H. Jagtap, Indian J. Chem. 39A (2000) 1145.
[15]. H.W. Florey, Antibiotics II, Oxford medical publications. U.K. (1949) 1476
[16]. S.G. Shirodkar, P.S. Mane, T.K. Chondhekar, Indian J. of Chem. 40A (2001) 1114.
[17]. R. Rajavel, M. Senthil, Vadivu, C Anitha, E-J. Chem. 5 (2008) 620.
[18]. Gangadhar B. Bagihalli, Prakash Gouda Avaji, Prema S. Badami, Sangamesh Patil, J. Coord. Chem. 61 (2008) 2793
[19]. Jarahour A.A. and M. Motamedifar, K. Pakshir, N. Hadi, Z. Zarei, Molecules. 9 (2004) 815.
[20]. I.M. Awad, A.A. Aly, A.M. Abdel Alim, R.A. Abdel Aal, S.H. Ahmed, J. of Inorg. Biochem. 33 (1998) 77.
[21]. A.R. Sarkar, S. Mandal, Synth. React. Inorg. Met.-Org. Chem. 80 (2008) 1477.
S.J. Swamy, A. Dharma Reddy, J. Indian Chem. Soc. 77 (2000) 336.
[22]. Salib Kar, S.M. Elsayed, A.M. Elshabiny, Synth. React. Inorg. Met.-Org.Chem. 21 (10) (1990) 1511.
[23]. P.P. Hankare, P.H. Bhoite, P.S. Battse, K.M. Garadkar, A.H. Jagtap,Indian J. Chem. 39A (2000) 1145.
[24]. S.G. Shirodkar, P.S. Mane, T.K. Chondhekar, Indian J. of Chem. 40A (2001) 1114.
[25]. R. Rajavel, M. Senthil, Vadivu, C Anitha, E-J. Chem. 5 (2008) 620.

[26]. Gangadhar B. Bagihalli, Prakash Gouda Avaji, Prema S. Badami,Sangamesh Patil, J. Coord. Chem. 61 (2008) 2793.
[27]. J. Iqbal, S. Sharfuddin, M. Imran, S. Latif, Turk. J. Biol. 30 (2006) 1.
[28]. X. Chen, J. Zhang, H. Zhang, Z. Jiang, G. Shi, Y. Li, Y. Song, Dyes Pigm. 77 (2011) 223–228.
[29]. Khalood’s Abou-Melha, J. Coord. Chem. 61 (2008) 2053.
[30]. M. Thankamony, K. Mohanan, Ind. J. Chem. 46A (2007) 249.
[31]. Gehad Geindy Mohamed et al, Turk. J. Chem. 30 (2006) 361.
[32]. Abdul hakim, A. Ahmed. A. Salima. BenGuzzi, Soad. Agumati, J. of Sci. and It’s Appl. 2 (2008) 83.
[33]. Srinivasan Durairaja, Sangeetha Srinivasan, P.Lakshamana Perumalsamy, Electronic Journal of Biology. 5 (1) (2009) 5.
Figure captions:
Scheme 1: Synthesis of Schiff base and metal complexes.
Figure 1: UV-Visible spectra of Schiff base ligand [HL]
Figure 2: FTIR spectra of Schiff base Ligand [HL]
Table captions:
Table 1 Analytical and Physical data of the compounds studied.
Table 2 FTIR spectral data.
Scheme 1: Synthesis of Schiff base and metal complexes.
O H
H
O
+ O N H 2NH 2
R E F L U X
E t O H
O H N
H
O N
H
O H
3
H r s .
S y n t h e s is o f S c h iff B a s e
Table 1: Analytical and Physical data of the compounds studied.
Sr.
No.
Compound
Mole. formula
(Mol. wt)
Colour
M.P./
Decompositio
n
temp.0
C
Yield
%
1 HL C26H20N2O3
(408)
Faint
Yellow
215 95
2 HL-Co C26H20N2O32Co.4H2O
(870)
Yellowish
Brown
>295 83
3 HL-Cu C26H20N2O32Cu.4H2O
(822)
Radish
Brown
>295 85

R E F L U X
E t O H
O H N
H
O N
H
O H
3
H r s .
2
M + +
O N
H
O N
H
O
M
M
S y n t h e s i s o f S c h if f b a s e m e t a l c o m p l e x
Table 2: FTIR spectral data.
Table No-3 Biological activity and its Metal complexes
Name of
Compounds
ν(C=N) ν(C-O) ν(M-O) ν (M-N) ν(O-H)
HL 1620 1188 - - 3380
HL -Co 1605 1148 460 521 3357
HL -Cu 1602 1145 465 544 3360
Name of
compd.
Conc.
µg / mL
Staphylococcus
Aureus
Pseudomonas
Aeruginosa
HL1
2 - -
4 + -
6 + +
8 + +
HL-Co
2 + -
4 + -
6 + +
8 + +
HL-Cu
2 ++ +
4 ++ ++
6 ++ ++
8 +++ ++

MMJ-HL-1
Name
Sample 069Bywcs DateWednesday, February062013
Description
4000 4503500 3000 2500 2000 1500 1000 500
90
21
25
30
35
40
45
50
55
60
65
70
75
80
85
cm-1
%T
1283.27cm-1, 22.48%T1491.33cm-1, 26.99%T
833.47cm-1, 27.30%T
1188.48cm-1, 30.19%T
1620.12cm-1,30.24%T
1504.87cm-1,33.30%T
740.27cm-1, 33.41%T
749.32cm-1,34.09%T
1262.75cm-1, 37.98%T
1573.70cm-1, 46.30%T
1150.19cm-1, 52.78%T
1455.99cm-1, 53.54%T
848.86cm-1, 54.67%T
544.10cm-1, 57.63%T1411.08cm-1, 58.73%T
1110.17cm-1, 61.99%T
1104.06cm-1, 62.01%T
521.29cm-1, 62.36%T
911.06cm-1, 62.55%T
981.90cm-1,62.69%T
1362.91cm-1,63.15%T
533.87cm-1, 63.35%T
3052.65cm-1, 63.90%T
2990.19cm-1, 64.52%T
1299.53cm-1, 64.53%T
2909.76cm-1,65.30%T
878.63cm-1, 66.19%T
1162.96cm-1,67.35%T
780.24cm-1, 68.01%T
714.72cm-1, 68.87%T
1032.14cm-1, 72.20%T
1011.32cm-1, 74.73%T
935.77cm-1, 76.77%T
1897.27cm-1, 77.39%T
464.90cm-1, 79.95%T944.70cm-1, 80.18%T1319.97cm-1, 81.48%T
651.62cm-1, 81.64%T
497.55cm-1,82.89%T
1684.50cm-1, 83.14%T
623.42cm-1,83.83%T
Figure 2 FTIR spectra of Schiff base Ligand [HL].

International Journal of Engineering and Science Invention (IJESI)

More Related Content

What's hot (18)

Similar to International Journal of Engineering and Science Invention (IJESI) (20)

Recently uploaded (20)

International Journal of Engineering and Science Invention (IJESI)