Chemical Synthesis, Spectral Characterization and Antimicrobial Studies on Complexes of Ni(II), Cu(II) and Zn(II) with N, N-di (o-hydroxybenzenoylmethylene) Ethylenediamine
The Schiff’s base ligands and their complexes with Ni(II), Cu(II) and Zn(II) were synthesized and characterized by elemental analysis molar conductivity, infrared and ultraviolet-visible spectroscopy and magnetic susceptibility measurements. The ligands, ethylenedianil of o-hydroxyphenylglyoxal, C18H16N2O4, have been synthesized by condensation of ethylenediamine and orthohydroxyphenylglyoxal. The metal complexes were prepared by mixing of saturated solutions of ligands and metal salts in appropriate molar ratio in acetone and methanol solvents. The study also confirmed the formation of mono-, di- and trinuclear isopolystructures of the complexes in square planar geometry except for Zn(II), which has tetrahedral stereochemistry. The synthesized ligands and their metal complexes were screened for their antimicrobial activities against two bacterial strains (Staphylococcus aureous and Xanthomonas holcicola), and two fungal strains (Aspergillus niger and Fusarium oxysporum) using a disc diffusion method. The tests showed that the complexes have higher antimicrobial activity than the free Schiff’s base.
Ali Mohammed Yimer,
Chemical Synthesis, Spectral Characterization and Antimicrobial Studies on Complexes of Ni(II), Cu(II) and Zn(II) with N, N-di (o-hydroxybenzenoylmethylene) Ethylenediamine, American Journal of BioScience. Special Issue: Chemical Biology.
Vol. 2, No. 6-1,
2014, pp. 22-34.
Aminkhani, A., L. A. Saghatforoush, F. Khabari, and S. Ghammamy, 2008. Synthesis and characterization of a new Mercury (II) complex with dissymmetric tetradentate Schiff base ligand: [Hg (pytABrsal)] Cl. Asian J. Chem., 20, 2809-2814.
Avaji, P. G., C. H. V. Kumar, S. A. Patil, K. N. Shivananda and C. Nagaraju, 2009. European Journal of Medicinal chemistry, doi:10.1016/j.ejmech.03.032.
Burger, K., 1973. Coordination Chemistry Experimental Methods, London Bult/ Worths and Co publishers Ltd.
Canpolat, E. and M. Kaya, 2004. Studies on mononuclear chelates derived from substituted Schiff-base ligands (part 2): synthesis and characterization of a new 5-bromosalicyliden paminoacetophenone oxime and its complexes with Co(II), Ni(II), Cu(II) and Zn(II) J. Coord. Chem. 123.
Chakravarty, A. R., A. P. Nreddy, B. K. Santra and A. M. Thomas, 2002. Copper Complexes as Chemical Nucleases, J. Indian. Chem. Sci., 114, 319-401.
Chandra, S. and J. Sangeetika, 2004. EPR and electronic spectruml studies on copper(II) complexes of some N-O donor ligands J. Indian Chem. Soc, 81, 203-206.
Chaurasia, M. R., Miss Prema Shukla and N. K. Singh, 1982. Mixed Ligand Complexes of N- 6-methyl benzothiazol-2-yl-salicylaldimine & 2- methylbenzimidazole with Cu(II), Ni(II), Co(II), Mn(II), VO(II), Zn(II), Cd(II) and Hg(II). Journal of Chemical Sciences, 110-114.
Chohan, Z. H., A. Munawar and C. T. Supuran, 2001. Transition metal ion complexes of Schiff’s-bases synthesis, characterization and antibacterial properties. Metal-based drugs, 8: 137-143.
Cotton, A.F. and G. Wilkenson, 1988. Advanced inorganic chemistry, 5th edition; John Wiley and Sons USA, 37-50.
Cozzi, P. G., 2004. Metal–Salen Schiff base complexes in catalysis: Practical aspects. Chem. Soc. Rev., 33, 410-421.
Cusumano, M., M. A. Messina, F.Nicolo, M. L. D. Pietro, A. Rotondo, and E. Rotondo, 2004. NMR Study of L-Shaped Quinoxaline Platinum(II) Complexes - Crystal Structure of [Pt(DMeDPQ)(bipy)](PF6)2, Eur. J. Inorg. Chem., 4710-4717.
Del Paggio, A.A., D.R. McMillin, 1983. Inorg. Chem. 22, 691.
Di Bella, S., I. Fragala, T. J. Marks and M. A. Ratner, 1996. Journal of American Chemical Society, 118,12747-12751.
Dioxon, M. and E. C. Webb, 1964. Enzyme, Green and Co. London 43pp.
Eichhorn, G. L. and L. G. Marzilli, 1994. Advances in Inorganic Biochemistry Models in Inorganic Chemistry, PTR prentice-Hall, Inc.
Ferrari, M. B., S. Capacchi, G. Pelosi, G. Reffo, P. Tarasconi, R .Albertini, S. Pinelli, P. Lunghi, 1999. Synthesis, structural characterization and biological activity of helicin thiosemicarbazone monohydrate and a Copper(II) complex of salicylaldehyde thiosemicarbazone Inorg. Chim. Acta, 286, 134-141.
Gao, W. T. and Z. Zheng, 2002. Synthesis Studies on Optically Active Schiff base ligands Derived from Condensation of 2-Hydroxyacetophenone and Chiral diamine, J. Molecules, 7. 511-516.
Hanna, W. G. and M. M. Moaead, 2001. Synthesis and Characterization and Antimicrobialo Activity of Co(II), Ni(II) and Cu(II) complexes with new Asymmetrical Schiff’s base ligand. Transition Metal Chemistry, 26, 644.
Harlal, S. and A. K. Varshney, 2006. Synthetic Structural and Biochemical Studies of Organotin (IV) with Schiff bases Having Nitrogen and Sulfur Donor Ligands, Bioinorganic Chemistry and Applications, 2006, Article ID 23245, 1-7.
Houghton, R. P., 1979. Metal complex in Organic chemistry, 1st Ed, 335.
Hughes, M. N., 1984. The Inorganic Chemistry of Biological Processes, second edition, Wiley.
Huheey, J. E., 1993. Inorganic Chemistry 4th edition, Harper Collins college Publishes, New York, 391-434.
Iqbal, M. S., A. H. Khan, B. A. Loothar and I. H. Bukhari, 2009. Medicinal Chemistry Research, 31-42.
Keypour, H., S. Salehzadeh and R. V. Parish, 2002. Synthesis of two Potentially Heptadentate (N4O3) Schiff base Ligand Derived from Condensation of Tris-(3-amino propyl)amine and Salicylaldehyde or 4-hydroxysalicylaldehyde Ni(II) and Cu(II) complexes of the former ligand, J. Molecules, 7, 140-144.
Kirshener, S., Y. K. Wei, D. Francis and J. H. Bergman 1966. Anticancer and potential antiviral activity of complex inorganic compounds. J. Med. Chem. 9: 369-372.
Lever, A.B.P, 1984. Inorganic Electronic spectroscopy, Elsevier, New York.
Kojima, M., H. Taguchi, M. Tsuchimoto and K. Nakajima, 2003. Coordination Chemistry Reviews. 237, 183-196.
Long, N. J., 1995. Organometallic compounds for nonlinear optics: the search for en-lightenment. Angewandte Chemie International Edittion, 34, 21.
Madhu ,N. T. and P. K. Radhakrishnan, 2001. Synthesis and Reaction of Inorg. Met.-Org. Chem. 31, 315.
Mahler, H. R. and E. H. Cordes, 1966. Biological Chemistry, New York, Harper and Rowe. 54.
Majumder, A., G. M. Rosair, A. Mallick, N. Chattopadhyay, S. Mitra, 2006. Synthesis, structures and fluorescence of nickel, zinc and cadmium complexes with the N, N,O-tridentate Schiff base N-2- pyridylmethylidene-2-hydroxy-phenylamine Polyhedron, 25, 1753-1762.
Mapari, A. K. and K. V. Mangaonkar, 2011. Synthesis, Characterization and Antimicrobial Activity of Mixed Schiff Base Ligand Complexes of Transition Metal (II) ions. Int. J. Chem.Tech. Res. Vol.3, No.1 : 477-482.
Mitsunobu, N., K. Chitoshi, U. Hiotmi, Y. Kazushige and Y. Akio, 2005. Crystal Structure of 8-Hydroxyquinoline-2-carboxylicacid Copper (II) Complexes, Analytical Sciences, 21, 115-116.
Pandeya, S. N., D. Sriram, G. Nath and E. Clercq De, 1999. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives, Pharm. Acta Helv, 74, 11.
Ravanasiddappa, M., T. Sureshg, K. Syed, S. C. Radhavendray. C. Basavaraja and S. D. Angadi, 2008. E-J. Chem., Transition Metal Complexes of1, 4(2'-Hydroxyphenyl-1-yl) di-iminoazine: Synthesis, Characterization and Antimicrobial Studies, 5(2), 395-403.
Reddy, V., N. Patil and S. D. Angadi, 2008. Synthesis, Characterization and Antimicrobial Activity of Cu(II), Co(II) and Ni(II) Complexes with O, N, and S Donor Ligands, E-J. Chem., 5(3), 577-583.
Rosenberg, B., 1971. Some biological effects of platinium compounds: new agents for the control of tumours. Platinum Metal. Rev. 15: 42-51.
Sender, E. G., L. D. Wright and D. B. J. McCormick, 1965. Evidence for function of a metal ion in the activity of dihydroorotase from Zymobacterium oroticum. Biol. Chem. 240: 3628-3630.
Sharma, P. K., A. K. Sen, K. Singh and S. N. Dubey, 1997.Electronic spectrum and Transitions, J. Indian Chem. Soc. 74, 446.
Singh, K., M. S. Barwa and P. Tyagi, 2007. Synthesis and characterization of cobalt(II), nickel(II), copper(II) and zinc(II) complexes with Schiff base derived from 4-amino-3-mercapto-6-methyl-5- oxo-1,2,4-triazine Eur. J. Med. Chem, 42, 394-402.
Sonmez, M. and M. Sekerci, 2002. Synthesis and Characterization of Zn(II), Co(II),Ni(II) and Cu(II) Schiff basees Complexes from 1-Amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one with Salicylaldehyde, polish. J. Chem., 76, 907-914.
Spinu, C. and A. Kriza, 2000. Co(II), Ni(II) and Cu(II) complexes of bidentate Schiff‘s bases. Acta Chimica Solvenica, 47.
Steinhardt, J. and S. Beychok, 1964. The Proteins, 2nd ed. New York, Academic Press. 261-276.
Tarafder, M. H., N. Saravanan, K. A. Crouse and A. M. Ali, 2001.Coordination Chemistry and Biological Activity of Ni(II) and Cu(II) ion Complexes with Nitrogen-sulphur Donor Ligands Derived from S-benzyldit, Transition Metal Chemistry, 26, 613-618.
Temel, H., T. Taskm and M. Sekerci, 2002. XVI. National Chemistry Congress , Konya, Turkey, AN-49.
Upadhyay, R. K. and A. Rani, 1989.Some metal chelates of ketoanils, III.Acta Chem.Hung.126 (6), 767-773.
Upadhyay, R. K. and S. Sharma, 2007. Study in spin-crossover phenomenon in complexes of long chain ketoanils with active methylene group(s) with Fe(II) and Fe(III). PhD.thesis, C.C.S., University, Meerut.
Upadhyay, R. K., 1995.Studies of some metal chelates of ketoanils, IV.J. Indian Chem.Soc, 589.
Vigato, P. A. and S. Tamburini, 2004. Coordination Chemistry Reviews, 248
Vukadin, M. L., V. Ljijanas, M. S. Katalin and C. Valerijal, 2003. Transition Metal Complexes with Thiosemicarbazide-based Ligands. Part 46-Synthesis and Physico- Chemical Characterization of Mixed Ligand Cobalt (III) complexes with Salicylaldehyde semi-thiosemi and Isothiosemicarbazone and Pyridine, J. Serb. Chem. Soc., 68, 919-927
Williams, D. R., 1972. Metals, ligands and cancer. Chem. Rev. 72: 203-213.