Synthesis, Characterization, Metal ion intake and Antibacterial Activity of Schiff base Complexes of Cu(II),  Ni(II)and Co(II) using

di-α-formylmethoxy bis (3 pentadecenylphenyl) methane (DFMPM) and aniline

 

Jisha. M. J¹, C. Isac Sobana Raj²*

¹Department of Chemistry, Christian College, Kattakada, India-695572

²Department of Chemistry and Research, N. M. Christian College, Marthandam, India-629165.

 

ABSTRACT:

Cardanol, a naturally occurring C₁₅ unsaturated aliphatic chain substituted phenol derived from cashew nut shell liquid (CNSL) was used for the preparation of Schiff base ligand using aniline. This preparation involved (a) the conversion of cardanol into bis (3-pentadecenyl phenol) methane (BPPM) using formaldehyde. (b) bis (3-penta decenyl phenol) methane into di -α -formylmethoxy bis (3-pentadecenyl phenyl methane). DFMPM on treatment with epichlorohydrin followed by the action of sodium periodate. (c) DFMPM to Schiff base ligand with aniline and finally (d) Schiff base complexes with Cu (II), Ni (II) and Co (II) metal salts. The ligand and complexes were characterized by IR, UV- Visible ,¹H NMR and elemental analysis, melting point, conductivity, metal ion intake and the antibacterial activity was studied. The conductance measurements indicate that all the complexes of non electrolytes. The infrared spectra indicate the coordination of imino nitrogen and M-N bonds. UV -Visible spectra provide structural details of these complexes.¹H NMR data is also consistent with IR spectral data. The results indicate that the complexes of Cu (II), Ni (II), Co (II) are hexa coordinated and have moderate antibacterial activity.

 

 

 

1. NTRODUCTION:

Cardanol, a distillate of cashew nut shell liquid (CNSL) differs in its reactivity with formaldehyde and is used for the development of substituted phenolic resins and various other valuable industrial products (Pillai et al., 1990., John et al., 2001., Prabhakaran et al prepared by the reaction between cardanol and formaldehyde in equimolar ratio in the presence of 3 % hydrochloric acid solution at 90-95⁰C for 2hours. The phenolic group of obtained. DFMPM undergoes condensation reaction with aniline a Schiff base ligand was BPPM was converted to diglycidylether with epichlorohydrin, which on treatment with sodium periodate, di--formylmethoxy bis(3-pentadecenylphenyl) methane (DFMPM) was obtained. Schiff base ligand formed Schiff base metal complexes with Cu(II), Ni(II) and Co(II) metal salts.

 

The ligand and complexes were characterized by IR, UV-visible H NMR and elemental analysis, melting point, conductivity; metal ion intake and antibacterial activity were studied. The result indicates all the complexes of Cu(II), Ni(II) and Co(II) are hexa coordinated having moderate and antibacterial activity. The metal ion intake indicates the ligand can be used for the extraction of these metals from water.

 

2. MATERIALS AND METHODS:

2.1 Chemicals:

All chemicals employed in the present study were of analytical grade. Solvents employed were either of 99% purity or purified by known laboratory procedures.

 

2. 2 Elemental Analysis:

Micro analysis of carbon, hydrogen and nitrogen contents present in the samples were recorded on Perkins Elmer Elemental analyzer (2400). In the micro analysis, sample weighing 10mg concealed in a tin capsule was injected in the instrument and the computerized elemental percentage was obtained.

 

2. 3 Metal ion intake:

The metal ion intake during complexation was determined by standard. (Vogel, 1978) methods using EDTA.

 

2. 4 Conductivity Measurements:

The molar conductivities of the complexes in DMSO solutions (10-3M) at room temperature were measured using direct reading conductivity meter, Systronics conductivity bridge type 305.

 

2. 5 Electronic Spectra:

Electronic spectra of the ligands and its complexes were recorded in various solvents using Perkins Elmer lamda-25 uv /visible spectrometer in the range of 200-1100 nm.

 

2. 6 Magnetic Susceptibility Measurements:

Magnetic susceptibility measurements of the powdered sample were carried out by using Gouy's method at Room temperature.  Mercuric tetra (thiocyanato) cobaltate (II), Hg [Co (NCS) ₄] was used as calibrant.

 

2. 7 Infrared Spectra:

The spectra were recorded in PE-IR-2000 spectrometer in the ranges 4000-400cm-1. Potassium bromide pellet method was employed for sample preparation.

 

2. 8 NMR Spectra:

The ¹H NMR spectra of the ligand and complexes were recorded in CDCl₃ and 6 DMSO-d using AMX-300 MHz PT NMR spectrometer using TMS as the internal standard.

 

2. 9 Powder XRD:

The XRD pattern of the complexes was recorded on a Shimadzu XD-3 diffractometer using Cu-K radiation (=1.54A⁰).

 

2. 10 SEM Analysis:

The surface morphology of the complexes was studied using JSM- 5610 scanning electron microscope.

 

2. 11 Thermal Analysis:

Thermo gravimetric and differential thermal analyses of the complexes were recorded on a Perkin-Elmer-7 series thermal analyser, with a heating rate of 10⁰C / minute using nitrogen atmosphere.

 

2. 12 Antibacterial Activity:

The invitro growth inhibitory activity of the complexes were tested against bacteria E. coli, Klebsiella, Pseudomonas aeruginosa, (gram-ve) Staph. aureus and Bacillus cereus (gram - +ve) by disc diffusion method using agar as nutrient (Pelezar et al., 1998). The standard drug Gentamycin dissolved in DMSO which acts as control was also tested at the same concentration under conditions similar to that of complexes.

 

2. 13 Synthesis of Schiff base ligand with DFMPM and Aniline:

The synthesis of Schiff base ligand was carried out by reported methods (Borisova et al., 2007., Lakshmi et al., 2011). Ethanolic solution of DFMPM and aniline were taken in RB flask in 1:2 molar ratios and refluxed for an hour.  The reaction mixture was poured in ice, a yellow compound of Schiff base ligand was obtained (Isac Sobanaraj et al., 2011. The precipitated yellow compound was filtered, washed with water and dried over anhydrous calcium chloride. The crude sample was recrystalised from 50% absolute alcohol. yield = 62%.  Melting point 228⁰C

 

2, 14 Preparation of Schiff Base Metal complexes:

The metal complexes of the ligand were prepared by adding aqueous solution of Cu(II) nitrate, Ni(II) nitrate and Co(II) nitrate, to the ligand in 1:2 molar ratios and refluxed for about twelve hours at 80 - 85⁰C (Mishra and Mishra., 2011). The final product was filtered washed with ethanol, diethylether and hot water, and finally dried under vacuum at 90⁰C. Yield = 57-61%.

 

2. 15 Estimation of Metal ion intake:

The filtrates obtained in the above methods were collected. The collections where used for the estimation of metal ion intake for complexation using standard methods (Vogel., 1978).

 

3. RESULTS AND DISCUSSION:

All the metal complexes are coloured solids, stable towards air, and have high melting are soluble in DMF, CDCl₃ and DMSO.

 

3. 1 Elemental Analysis:

The analytical data suggested that all the complexes are mononuclear with the ligand coordinated to the central metal atom. The stoichiometry (Sulekh et al., 2007) and physical characteristics are given in the table 1.

 

3. 2 Molar Conductivity:

The observed molar conductance of complexes in 10^-3 M DMF indicate non-electrolytic nature of complexes (Prasad and Mathur., 2011). The low conductivity values of complexes suggest the nitrato groups are involved in coordination and the conductivity values were slightly higher than for non-electrolytes.  This may be due to the partial solvolysis of the complexes in DMF medium. Molar conductance of complexes was shown in Table 2

 

Table 1. Physical characteristics and analytical data of the complexes

Compound	Yield %	Colour	Mole. Formula	Mole. Wt.	Melting Point	Elemental Analysis Found(Calcd)%
						C	H	N
Ligand(L) (C59H82N2O2)	62	Brown	C59H82N2O2	850	228	83.24	9.58	3.31
						(83.29)	(9.64)	(3.29)
[Cu(L)2(NO3)2]	60	Light Green	C118H164N6O10Cu	1887.54	>250	74.93	8.57	4.38
						(75.01)	(8.68)	(4.36)
[Ni(L)2(NO3)2]	56	Pale Green	C118H164N6O10Ni	1882.69	>250	75.01	8.68	4.38
						(75.21)	(8.71)	(4.46)
[Co(L)2(NO3)2]	57	Brown	C118H164N6O10Co	1882.93	>250	74.94	8.58	4.39
						(75.2)	(8.7)	(4.46)

 

Table.2 Molar Conductance data of the Complexes

Compound	Molar Conductance Ohm-1 cm2 mol-1
Ligand (L) (C59H82N2O2)
[Cu (L)2(NO3)2]	16
[Ni (L)2 (NO3)2]	15
[Co (L)2 (NO3)2]	15

 

3. 3 IR Spectra:

The selected IR spectral data of the ligand and complexes are given in Table 3.

 

Table.3 Selected FTIR frequencies(cm^-1) of the Ligand and Complexes

Ligand/Complex	O-H (H2O)	C-O	C-H	C-N	M-N	M-O
Ligand (L)		2854.3	2926.2	1601.7	-	-
(C59H82N2O2)
[Cu (L)2(NO3)2]	3445.5	2852	2926	1630.5	693	-
[Ni (L)2 (NO3)2]	3384.7	2800	2910	1619.1	630.7	-
[Co (L)2 (NO3)2]	3360.3	2852.6	2923.8	1600	772	-

 

In the FTIR spectrum of the ligand, the absorption at 774.2 cm^-1 was due to the vibration of aromatic hydrogens. The absorptions at 794.9cm^-1 and 872.8 cm^-1 indicated the substituted aromatic compound. The absorptions at 1049.2 cm^-1, 1158.1 cm^-1, 1258.1 cm^-1, 1448.1 cm^-1, 1584.0 cm^-1 were due to the presence of aliphatic side chain, CO stretching vibration, stretching vibration of COC bond, presence of CH₂ group and skeletal in plane vibration of C = C bond respectively.  The presence of C = N bond, O C group are confirmed by the absorption at 1601.0 cm^-1, 2854.3 cm^-1 respectively. Also the absorptions at 2996.2 cm^-1 was due to the vibration of CH2 group (Raman et al., 2001) and absorption at 3008.1 cm-1 was due to the CC bond stretching of the aromatic ring. The FTIR spectrum the ligand was compared with the spectra of complexes.   The characteristic absorption bands3360.3 cm^-1 – 3445.9 cm^-1 were attributed to OH group of the lattice water (or) coordinated water. The absorption bands in the range 2852.6 cm-¹ -12585 cm^-1, 2926.6 cm^-1 – 2923.8 cm^-1 and 1630 cm^-1– 1563.3 cm^-1 were assigned to O – C –CH2, and –C=N bonds respectively. The absorption at 755.6 cm^-1, 984.7 cm^-1, 1029.5 cm^-1, 1029.6 cm^-1 were due to the coordination of nitrato group with central metal atom (Devi and Indrasenan., 1987). All the complexes showed absorption in the range 693 cm^-1, 630.7 cm^-1, 670.3 cm^-1, 682.6 cm^-1 and 682.6 cm^-1 indicated the presence M-N bond.

 

Fig.1 FTIR Spectrum of Ligand

 

Fig. 2 FTIR Spectrum of Cu(II) Complex of Ligand

 

Fig. 3 FTIR Spectrum of Ni(II) Complex of Ligand

 

Fig.4 FTIR Spectrum of Co(II) Complex of Ligand

3. 4 UV – Visible Spectra:

Nature of the ligand field around the metal ions has been derived from UV-visible spectra. The UV-visible spectra of ligand showed three peaks around 232 nm, 323nm, 448nm which were assignable to π-π * and n – π* transition (Srikanth and Kurup, 2003). The UV-visible absorption of the Cu(II) complex showed three spectral bands at 285 nm, 380nm and 446 nm. The band at 285 nm belonged to the charge transfer. The other 2 spectral bands were due to E_2g T_2g transition which is conformity with octahedral geometry (Shajalan, 2007) to Cu(II) complex. The broadness and the position of the band favours distorted octahedral geometry for Cu(II) complex due to Jahn-Teller effect. The UV-visible absorption spectrum of Ni(II) gave three absorption bands at 268 nm, 332 nm and 405 nm.  These bands were assignable to 3A_2g ,3T_2g(F),3A_2g(F) 3T_1g(F) and 3A_2g 3T_1g(P) transition is in assignment with octahedral arrangement for Ni(II) complexes. Similarly, the UV-Visible spectrum of Co(II) complex displayed three bands at 256nm, 290 nm and 375 nm. These have been assigned to 4T_2g(F) 4A_2g, T_1g(F) A2g(F) and 4T_1g(F) 4T_2g(P) transitions. These transitions are in agreement with octahedral arrangement for Co(II) ion (Al-Bayati et al., 2011). UV- Visible spectra of complexes are given in Table.4

 

Table 4.  UV-Visible Spectra of the ligand and complexes

Ligand/ Complex	λ max (nm)
Ligand (L) (C59H82N2O2)	232	323	448
[Cu (L)2(NO3)2]	285	380	446
[Ni (L)2 (NO3)2]	268	332	405
[Co (L)2 (NO3)2]	256	290	375

 

3. 5 Magnetic Susceptibility Measurements:

The magnetic susceptibility values of the complexes are shown below in Table 5. The Cu(II) complex exhibited magnetic moment of 1.8 BM indicating greater distorted octahedral geometry of the complex. (Guadasi et al., 2006)   Co (II) complex had magnetic moment of 4.9 BM indicated the high spin nature of the complex and have octahedral geometry. The Ni (II) complex exhibited the magnetic moment value of 2.9 BM indicating octahedral coordination (Guadasi et al., 2006, Canpolat et al., 2006).

 

Table 5. Magnetic Susceptibility of Complexes

Ligand/ Complex	Magnetic Susceptibility (BM)
[Cu (L)2(NO3)2]	1.8
[Ni (L)2 (NO3)2]	2.9
[Co (L)2 (NO3)2]	4.9

 

3. 6 ¹H NMR Spectra:

The 1H NMR spectrum of ligand exhibits a multiplet at 7.008 – 7.173 ppm is due to substituted aromatic ring protons (Chandra et al., 2005). The presence of H – C = N group is indicated by the singlet at δ = 8.305 ppm.  A signal at δ = 1.22ppm – 1.242 ppm indicate the presence of –CH2– protons.  The multiplet at δ=6.489 ppm -  δ = 6.605 ppm and δ= 3.438 ppm - δ = 3.990 ppm are due to the olifinic protons of the side chain and – OCH2 group of the ligand respectively. On the basis of above studies, the proposed structure of ligand and complexes may be presented as follows (fig 5 and fig 6)

 

Fig. 5 Structure of ligand

 

Fig. 6 General Structure of Schiff base metal complex of ligand M = Cu(II) and Co(II)

 

Fig. 7 The ¹H NMR Spectrum of Ligand

 

3. 7 SEM Analysis:

The surface morphology of the complexes has been examined using scanning electron microscope. The SEM images of Co(II) complexes are given below. The SEM images showed that all the complexes are micro crystalline in nature. Careful examination of the single crystal, clearly indicated the nanoscale size of the single crystal of the complexes. In ethanol solvent they showed bead like appearance but the powdered samples showed rough and amorphous nature.

 

 

3. 8 X-ray Diffraction Analysis:

The powder XRD for the Co (II) was performed.  The respective diffractogram is given in Fig.10 The grain size of the complexes was calculated using Scherre’s formula. The calculated grain size is in the range of 14.59 nm.  This value suggested the crystals of the Co(II) complexes are in nano size.  These values are closely in agreement with SEM images of the above complexes

 

Fig 8 SEM image of Schiff base complex of Co (II) in ethanol

 

Fig 9.SEM image of Powder Sample of Co(II) complex

 

Fig. 10 XRD Spectrum of Co (II) Complex

 

3. 9 Thermal Analysis:

The TG/DTA analysis of Co (II) complex was carried out and the TGA graphs were shown in Fig 11. The result showed that the complex decompose in three steps. In the first step with in the temperature range 76⁰C-257⁰C a loss of mass 10% suggests the loss of hydrate water molecule. In the second step with in the temperature range 365⁰C to 478⁰C, a loss of mass corresponds to the loss of nitrato group. In the final step around 478⁰C to 739⁰C is due to be loss of ligand molecule and CuO is obtained as the final product (Patel et al., 2000). The results are in good accordance with the composition of the complexes.

 

3. 10 Metal ion intake:

The metal ion inateke data of the complex with ligand is given in table 6. Nature of the ligand and the chelate effect were the factors involved in complexation. The metal complexing nature of Schiff base ligands depend not only electron donor atoms of the ligand groups, but also their accessibility to the metal ion. Hence, steric hindrance by the polymeric matrix and the hydrophobic nature of the polymeric ligand units can limit the chelating reaction (Tuncel et al., 2008). This study indicated that the metal ion intake decreased from Cu(II) > Co(II) > Ni(II). This order can be explained by Pearson proposal, hard acids prefer to combine with hard base and soft acids prefer to combine with soft base.

 

3. 11 Antibacterial Activity:

The results of antibacterial activity substantiate the findings of earlier researchers, that biologically in active compounds become active and less biologically active compounds become more active upon coordination (Destri et al., 1999, Kaya et al., 2001, Thamizharasi et al., 2008). Such enhancement in biological activity of metal complexes can be explained on the basis of Overtone's concept and chelation theory. Antibacterial activities of the ligand, complexes and standard drugs were screened by disc diffusion method in DMSO as solvent. The results of antibacterial study are given in Table- 7. The antibacterial activity was estimated based on the size of inhibition zone in the discs. Under identical conditions the Schiff base complexes of copper (II), Cobalt (II) and Nickel (II) had moderate antibacterial activities against these bacteria.

 

Fig. 11 Thermo analytic curve for Cu(II) complex of ligand

 

Table .6 Metal ion intake of the Complexes with Ligand

Compound	Metal ion intake meq/g
[Cu(L)2(NO3)2]	0.584
[Ni(L)2(NO3)2]	0.7014
[Co(L)2(NO3)2]	0.8075

 

Table 7.  Antibacterial activity data of ligand and complexes.

Ligand/Complex	Klebsiella	S. aerus	E-coli	P. aeruginosa	B. Cereus
C59H82N2O2 (L)	++	++	++	++	++
[Cu (L)2(NO3)2]	++	15mm	++	++	14mm
[Ni (L)2 (NO3)2]	10mm	8mm	++	++	++
[Co (L)2 (NO3)2]	19mm	20mm	12mm	18mm	14mm
Control (Entamycin)	21 mm	10 mm	16 mm	23 mm	21 mm

(++)1-5 mm less active

 

4. CONCLUSION:

Schiff base transition metal complexes Cu(II), Ni(II) and Co(II), were synthesised from cardanol using aniline were clearly described and characterized on the basis of analytical and spectral data. Metal ion take explained that the ligand can be effectively used for extraction of metal ion from waters. Antibacterial study showed that the copper (II), Ni (II) and Co (II) have moderate antibacterial activity. The present investigation suggests that all the metal complexes of the ligand bearing metal ion, phenolic moiety, unsaturated side chain, benzene ring, -N=CH- group have comparatively more biological activity. This study serves as a basis for the chemical modifications directed towards the development of new class of antibacterial agents.

 

5. CONFLICT OF INTEREST:

The authors declare no conflict of interest.

 

6. REFERENCES:

1.     Al-Bayati R.I.H, Mahdi F.R and Al-Amiery A.A.H., Synthesis, spectroscopic and Antimicrobial studies of Transistion metal   complexes of N-Amino Quinolone, British Journal of Pharmacology and Toxicology. 2011; 2(1): 5-11,

2.     Al-Shajalan, N.H., Antimicrobial activity and spectral, magenetic and thermal studies of some transition metal complexes of a schiff base hydrazone containing a quinoline moiety., Molecules, 12: 1080 – 1091. Molecules. 2007; 12(5): 1080-1091

3.     Borisova, N.E., Reshetova, M.D., Ustynyuk, Y.A., Metal free methods in synthesis of macrocyclic Schiff base. Chemical Reviews. 2007; 107(1: 46-79.

4.     Canpolat, E., Yeiazi, A., and Kaya, M., Synthesis and Characterization of Mononuclear Cobalt(II), Nickel(II), Copper(II), Zinc(II), Cadmium(II) and Dinuclear Uranyl(VI) Complexes with N, N-bis (2- {[(2,2-dimethyl-1,3-dioxolan-4- yl) methyl] amino} butyl) N′, N′-dihydroxyethanediimidamide Transition Metal Chemistry. 2006; 31: 653-657.

5.     Chandra, S., and Kumar, P., Spectral and magenetic studies on manganese(II), cobalt(II) and nickel(II) complexes with Schiff bases. Spectrochimica Acta Part A. 2005; 61: 219-224.

6.     Destri, S., Pasini, M., Pelizzi, C., Porzio, W., Predieri, G., and Vignali, C., Synthesis and Characterization of Conjugated   Polyazines and Polyazomethines Containing the Thienylene Moiety and Flexible Hydrocarbon Side Chains.Macro Molecules. 1999; 32: 353-360.

7.     Devi, S.G., Indrasenan, P., Uranyl nitrate complexes of some Schiff bases of 4- aminoantipyrine and certain carbonyl compounds Inorg. Chem. Acta. 1987; 13: 157- 160.

8.     Gudasi, K.B., Patil, M.S., Vadavi, R.S., Shenoy, R., Patil, S.A., and Nethaji. M., Crystal structure of 2-(2-hydroxy-3-methoxy, Phenyl] – 3- [2- hydroxyl – 3- methoxy benzylamino] -1, 2 – dihydro-quinazolin -4 (3H)-one and the synthesis, spectral and thermal investigation of its transition metal complexes. Transition Metal Chemistry. 2006; 31 (5): 586-592.

9.     Isac Sobana Raj. C., Christudhas, M., and Allen Gnana Raj, G., Synthesis, Characterization, Metal ion intake and Antibacterial Activity of Cardanol based Polymeric Schiff base Transition Metal Complexes using Ethylenediamine, J. Chem. Pharm. Res. 2011; 3(6):127-135.

10.   John, G., Masuda, M., Okada, Y., Yase, K., Shimizu, T., Nanotube Formation from Renewable Resources via Coiled Nanofibers. Advanced Material. 2001; 13: 715–718.

11.   Kaya, I., Vilayetoglu, A. R., and Mart, H., The synthesis and properties of oligosalicylaldehyde and its Schiff base poligomers. Polymer. 2001; 42: 4859 -4865.

12.   Lakshmi, B., Shivananda, K. N., Prakash, G. A., Synthesis of Co(II), Ni(II) and Cu(II) complexes from Schiff base ligand and reactivity studies with thermosetting epoxy Resin. Bull. Korean Chem. Soc. 2011; 32 (5): 1613-1619.

13.   Mishra, D. K., and Mishra, A. P., Synthesis structural characterization and biological significance of some novel Schiff base complexes with Co(II), Ni(II) and Cu(II). Int. J. Pharm. Res. Dev, 3(5) 24-31.

14.   Patel. K. N, Patel. N. H, Patel. K. M, Patel. M. N., Synthesis and Characterization of Cobalt(II), Nickel(II), Copper(II), Zinc(II) Mixed- Ligand Complexes. Synth. React.Inorg.Met.Org.Chem.2000; 30 (5): 921-930

15.   Pelezar, M.J., Chan, E.C.S. and Kreig, N.R., Microbiology. Fifth Edn; NewYork.1998

16.   Pillai, C. K. S., Manjula, S., Thermal characterization of cardanol-formaldehyde resins and cardanol-formaldehyde poly (methyl methacrylate) semi-interpenetrating polymer networks. Thermochimica Acta. 1990; 159: 255–266.

17.   Prabhakaran, K., Asha Narayanan, Pavithran, C., Cardanol as a dispersant plasticizer for an alumina/toluene tape casting slip. Journal of the European Ceramic Society. 2001; 21: 2873-2878.

18.   Prasad, R.N., and Mathur, M., Synthesis and characterization of Cr(III), Fe (III), Co(II), Ni(II), Cu(II) Zn(II) complexes of 2,14-dimethyl-3,15 di-n-propyl-1,4,13,16- tetrazacylitetracosa – 1, 3, 15- tetracne. J. Indian. Chem. Soc. 2011; 8: 415-419.

19.   Raman. N, Kulandaisamy. A, Shunmuga Sundaram. A., and Jeyasubramanian. K, Synthesis, spectral, redox and antimicrobial activities of Schiff base complexes derived from 1-phenyl-2,3-dimethyl-4-a  minopyrazol-5-one and acetoacetanilide. Transition Metal Chemistry. 2001; 26: 131-135.

20.   Ranjana Yadav and Deepak Srivastava., Statistical Design and Response Surface Technique for the Optimization of Cardanol Based Phenolic Polymer. Archives of Applied Science Research. 2012; 4 (5): 2261-2273.

21.   Sreekanth, A., and Kurup, M.R.P., Structural and spectral studies on four co- ordinated copper (II) complexes of 2-benoylpyridine N (4), N (4)-butane-1, 4-  diyl)57 thiosemicarbazone. Polyhedron. 2003; 22: (25-26). 3321-3332.

22.   Sulekh, C., Smriti, R., Monika, T and Gautam, A., Synthesis, spectroscopic and antimicrobial studies of Bivalent Nickel and Copper complexes of Bis (thiosemicarbazone). Bioinorga. Chem. Appl. 2007; 2007: 51483.

23.   Thamizharasi, S., Vasantha, J., Reddy, B. S. R., Synthesis, characterization and pharmacologically active sulfamethoxazole polymers. Eur. Polym. J. 2002; 38: 551-559.

24.   Tuncel, M., Ozbulbul, A., and Serin, S., Synthesis and characterization of thermally Stable Schiff base polymers and their copper(II), cobalt(II) and nickel(II) complexes. Reactive and Functional Polymers. 2008; 68: 292-306.

25.   Vogel, I. Text book of “Quantitative Inorganic Analysis”. 4th Edition, Longman, London,1978

26.   Isac Sobanaraj.C and Allen Gnana Raj. G. Blessy. C. Synthesis, Characterization and Biological evaluation of bidentate ligand with metal ions of Zr(IV) and Th(IV). Journal of Chemical and Pharmaceutical Research. 2016; 8(6):372-379

27.   C Isac Sobana raj. Synthesis and characterization of Bio active transition metal complexes of Zr(IV) and Th(IV) using DFMPM derived from Cardanol. Asian Journal of chemical and pharmaceutical research. 2015; 3(1): 208-214

 

 

 

Received on 14.08.2017         Modified on 18.09.2017

Accepted on 21.10.2017         © AJRC All right reserved