Synthesis and Theoretical Study of Zinc(II) and Nickel(II)-Complexes of 5-Methoxyisatin 3-[N-(4-chlorophenyl)thiosemicarbazone]

Authors

  • Fatma Kandermirli 1Department of Chemistry, Ni?de University, 51240, Ni?de, Turkey
  • Murat Saracoglu 2Faculty of Education, Erciyes University, 38039, Kayseri, Turkey
  • Gamze Bulut 3Department of Chemistry, Kocaeli University, 41380, Izmit, Turkey
  • Eno Ebenso 4Department of Chemistry, North West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa
  • Taner Arslan 5Department of Chemistry, Osmangazi University, 26480, Eski?ehir, Turkey
  • Asgar Kayan 3Department of Chemistry, Kocaeli University, 41380, Izmit, Turkey

DOI:

https://doi.org/10.5614/itbj.sci.2012.44.1.4

Abstract

Zinc(II) and nickel(II)-complexes of 5-methoxyisatin 3-[N-(4-chlorophenyl) thiosemicarbazone] (H2MICP) were synthesized and characterized by infrared, ultraviolet and 1H-NMR spectroscopies as well as elemental analysis. Model of H2MICP and its zinc(II) and nickel(II)-complexes were optimized with B3LYP method using 6-31G(d,p), 6-311G(d,p), 6-311++G(d,p), 6-311++G(2d,2p) basis sets. The calculated 1H-NMR, UV and IR spectra data were compared with experimental results. In addition to the Natural Bond Orbital (NBO) analysis of H2MICP and its Zinc(II) and Nickel(II) complexes, Fukui functions of H2MICP were also reported.

References

Pandeya, S.N., Sriram, D., Nath, G. & De Clercq, E., Synthesis, Antibacterial, Antifungal and Anti HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4-chlorophenyl) hiazol-2-yl] thiosemicarbazide, Eur. J. Pharma. Sci., 9, pp. 25-31, 1999.

Bauer, D.J. & Sadler P.W., The structure-activity relationships of the antiviral chemotherapeutic activity of isatin -thiosemicarbazone, Brit. J. Pharmacol. 15, pp. 101-110, 1960.

Levinson, W. & Helling, R., Inactivation of lambda phage infectivity and lambda deoxyribonucleic acid transfection by N-methyl-isatin f3-thiosemicarbazone-copper complexes, Antimicrob. Agents Chemother., 9, pp. 160-163, 1976.

Qu, J.Q., Sun, G.C., Wang, L.F. & Qu, L., Synthesis, Characterization, And Biological Activities of Some Transition metal(II) Complexes with the Thiosemicarbazone derived from 4-[1-(4-methylphenylsulfonyl)-1 H -indol-3-yl]but-3-en-2-one, Chem. Mat. Sci., 60(3), pp. 214-219, 2006.

Karali, N., G1/4rsoy, A., Kandemirli, F., Shvets, N., Kaynak, .F.B., -zbey. S., Kovalishyn, V. & Dimoglo, A., Synthesis and Structure-Antituberculosis Activity Relationship of 1H-indole-2,3-dione derivatives, Bioorg. Med. Chem., 15(17), pp. 5888-5904, 2007.

Saracoglu, M., Kandemirli, F., Kovalishyn, V., Arslan, T. & Ebenso, E.E., ETM-ANN Approach Application for Thiobenzamide and Quinolizidine Derivatives, J. Biomed. and Biotech., 2010, doi:10.1155/2010/693031, 12 pages, 2010.

Kandemirli, F., Arslan, T., Koksoy, B. & Yilmaz, M., Synthesis, characterization and theoretical calculations of 5-methoxyisatin-3-thiosemicarbazone derivatives, J. Chem. Soc. Pak., 31(3), pp. 498-504, 2009.

Parr, R.G. & Yang W., Density Functional Theory Of Atoms And Molecules, Oxford University Press. Oxford. 1989.

A.D. Becke, A New Mixing of Hartree-Fock and Local Density-Functional Theories, J. Chem. Phys., 98, pp. 1372-1377, 1993.

Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, Jr. J.A., , Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, -., Foresman, J.B., Ortiz, J.V., Cioslowski, J. & Fox, D.J., Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford CT, 2009.

Kandemirli, F., Arslan, T., Karadayn, N., Ebenso, E.E. & Koksoy, B., Synthesis and Theoretical Study of 5-methoxyisatin-3-(N-cyclohexyl)-Thiosemicarbazone and Its Ni(II) and Zn(II) complexes, J. Mol. Struc., 938, pp. 89-96, 2009.

Gorelsky, S.I., AOMix: Program for Molecular Orbital Analysis, University of Ottawa, Ottawa, Canada, 2009, http://www.sg-chem.net.

Gorelsky, S.I. & Lever, A.B.P., Electronic Structure And Spectra Of Ruthenium Diimine Complexes By Density Functional Theory and INDO/S. Comparison of the Two Methods, J. Organomet. Chem., 635, pp. 187-196, 2001.

Weinhold. F., Natural Bond Orbital Analysis Programs Theoretical Chemistry Institute and Department of Chemistry, University of Wisconsin, Madison, Wisconsin, 53706.

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