Synthesis, Spectroscopic, and Antimicrobial Studies on Bivalent Nickel and Copper Complexes of Bis(thiosemicrbazone)

Abstract

A series of metal complexes of Cu(II) and Ni(II) having the general composition [M(L)X2] with benzil bis(thiosemicarbazone) has been prepared and characterized by element chemical analysis, molar conductance, magnetic susceptibility measurements, and spectral (electronic, IR, EPR, mass) studies. The IR spectral data suggest the involvement of sulphur and azomethane nitrogen in coordination to the central metal ion. On the basis of spectral studies, an octahedral geometry has been assigned for Ni(II) complexes but a tetragonal geometry for Cu(II) complexes. The free ligand and its metal complexes have been tested in vitro against a number of microorganisms in order to assess their antimicrobial properties.

References

1. J. S. Casas, M. S. García-Tasende, and J. Sordo, “Main group metal complexes of semicarbazones and thiosemicarbazones. A structural review,” Coordination Chemistry Reviews, vol. 209, no. 1, pp. 197–261, 2000. View at: Publisher Site | Google Scholar
2. D. Mishra, S. Naskar, M. G. B. Drew, and S. K. Chattopadhyay, “Synthesis, spectroscopic and redox properties of some ruthenium(II) thiosemicarbazone complexes: structural description of four of these complexes,” Inorganica Chimica Acta, vol. 359, no. 2, pp. 585–592, 2006. View at: Publisher Site | Google Scholar
3. I. Kizilcikli, B. Ülküseven, Y. Daşdemir, and B. Akkurt, “Zn(II) and Pd(II) complexes of thiosemicarbazone-S-alkyl esters derived from 2/3-formylpyridine,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 34, no. 4, pp. 653–665, 2004. View at: Publisher Site | Google Scholar
4. N. K. Singh, S. B. Singh, A. Shrivastav, and S. M. Singh, “Spectral, magnetic and biological studies of l,4-dibenzoyl-3-thiosemicarbazide complexes with some first row transition metal ions,” Proceedings of the Indian Academy of Sciences: Chemical Sciences, vol. 113, no. 4, pp. 257–273, 2001. View at: Google Scholar
5. O. E. Offiong and S. Martelli, “Stereochemistry and antitumour activity of platinum metal complexes of 2-acetylpyridine thiosemicarbazones,” Transition Metal Chemistry, vol. 22, no. 3, pp. 263–269, 1997. View at: Publisher Site | Google Scholar
6. Z. Afrasiabi, E. Sinn, S. Padhye et al., “Transition metal complexes of phenanthrenequinone thiosemicarbazone as potential anticancer agents: synthesis, structure, spectroscopy, electrochemistry and in vitro anticancer activity against human breast cancer cell-line, T47D,” Journal of Inorganic Biochemistry, vol. 95, no. 4, pp. 306–314, 2003. View at: Publisher Site | Google Scholar
7. E. M. Jouad, G. Larcher, M. Allain et al., “Synthesis, structure and biological activity of nickel(II) complexes of 5-methyl 2-furfural thiosemicarbazone,” Journal of Inorganic Biochemistry, vol. 86, no. 2-3, pp. 565–571, 2001. View at: Publisher Site | Google Scholar
8. N. K. Singh and S. B. Singh, “Synthesis, characterization and biological properties of manganese(II), cobalt(II), nickel(II), copper(II), zinc(II), chromium(III) and iron(III) complexes with a new thiosemicarbazide derivative,” Indian Journal of Chemistry, vol. 40, no. 10, pp. 1070–1075, 2001. View at: Google Scholar
9. Z. Afrasiabi, E. Sinn, J. Chen et al., “Appended 1,2-naphthoquinones as anticancer agents 1: synthesis, structural, spectral and antitumor activities of ortho-naphthaquinone thiosemicarbazone and its transition metal complexes,” Inorganica Chimica Acta, vol. 357, no. 1, pp. 271–278, 2004. View at: Publisher Site | Google Scholar
10. N. K. Singh, A. Srivastava, A. Sodhi, and P. Ranjan, “In vitro and in vivo antitumour studies of a new thiosemicarbazide derivative and its complexes with 3d-metal ions,” Transition Metal Chemistry, vol. 25, no. 2, pp. 133–140, 2000. View at: Publisher Site | Google Scholar
11. S. Singh, N. Bharti, F. Naqvi, and A. Azam, “Synthesis, characterization and in vitro antiamoebic activity of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones and their palladium (II) and ruthenium (II) complexes,” European Journal of Medicinal Chemistry, vol. 39, no. 5, pp. 459–465, 2004. View at: Publisher Site | Google Scholar
12. S. Sharma, F. Athar, M. R. Maurya, F. Naqvi, and A. Azam, “Novel bidentate complexes of Cu(II) derived from 5-nitrofuran-2-carboxaldehyde thiosemicarbazones with antiamoebic activity against E. histolytica,” European Journal of Medicinal Chemistry, vol. 40, no. 6, pp. 557–562, 2005. View at: Publisher Site | Google Scholar
13. D. C. Quenelle, K. A. Keith, and E. R. Kern, “In vitro and in vivo evaluation of isatin $-\beta$-thiosemicarbazone and marboran against vaccinia and cowpox virus infections,” Antiviral Research, vol. 71, no. 1, pp. 24–30, 2006. View at: Publisher Site | Google Scholar
14. N. Bharti, F. Athar, M. R. Maurya, and A. Azam, “Synthesis, characterization and in vitro anti-amoebic activity of new palladium(II) complexes with 5-nitrothiophene-2-carboxaldehyde $N\left(4\right)$-substituted thiosemicarbazones,” Bioorganic and Medicinal Chemistry, vol. 12, no. 17, pp. 4679–4684, 2004. View at: Publisher Site | Google Scholar
15. B. J. A. Jeragh and A. El-Dissouky, “Synthesis, spectroscopic and the biological activity studies of thiosemicarbazones containing ferrocene and their copper(II) complexes,” Journal of Coordination Chemistry, vol. 58, no. 12, pp. 1029–1038, 2005. View at: Publisher Site | Google Scholar
16. E. Labisbal, K. D. Haslow, A. Sousa-Pedrares, J. Valdés-Martínez, S. Hernández-Ortega, and D. X. West, “Copper(II) and nickel(II) complexes of 5-methyl-2-hydroxyacetophenone $N\left(4\right)$-substituted thiosemicarbazones,” Polyhedron, vol. 22, no. 20, pp. 2831–2837, 2003. View at: Publisher Site | Google Scholar
17. R. V. Singh, N. Fahmi, and M. K. Biyala, “Coordination behavior and biopotency of N and S/O donor ligands with their palladium(II) and platinum(II) complexes,” Journal of the Iranian Chemical Society, vol. 2, no. 1, pp. 40–47, 2005. View at: Google Scholar
18. S. Chandra, Sangeetika, and A. Rathi, “Magnetic and spectral studies on copper(II) complexes of N-O and N-S donor ligands,” Journal of Saudi Chemical Society, vol. 5, no. 2, pp. 175–182, 2001. View at: Google Scholar
19. H. A. Tang, L. F. Wang, and R. D. Yang, “Synthesis, characterization and antibacterial activities of manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II) complexes with soluble vitamin ${\text{K}}_3$ thiosemicarbazone,” Transition Metal Chemistry, vol. 28, no. 4, pp. 395–398, 2003. View at: Publisher Site | Google Scholar
20. R. V. Singh, M. K. Biyala, and N. Fahmi, “Important properties of sulfur-bonded organoboron (III) complexes with biologically potent ligands,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 180, no. 2, pp. 425–434, 2005. View at: Publisher Site | Google Scholar
21. R. F. F. Costa, A. P. Rebolledo, T. Matencio et al., “Metal complexes of 2-benzoylpyridine-derived thiosemicarbazones: structural, electrochemical and biological studies,” Journal of Coordination Chemistry, vol. 58, no. 15, pp. 1307–1319, 2005. View at: Publisher Site | Google Scholar
22. A. E. Liberta and D. X. West, “Antifungal and antitumor activity of heterocyclic thiosemicarbazones and their metal complexes: current status,” Biometals, vol. 5, no. 2, pp. 121–126, 1992. View at: Publisher Site | Google Scholar
23. R. K. Agarwal, L. Singh, and D. K. Sharma, “Synthesis, spectral and biological properties of copper(II) complexes of thiosemicarbazones of schiff bases derived from 4-aminoantipyrine and aromatic aldehyde,” Bioinorganic Chemistry and Applications, vol. 2006, Article ID 59509, pp. 1–10, 2006. View at: Publisher Site | Google Scholar
24. B. N. Figgis and R. S. Nyholm, “A convenient solid for calibration of the Gouy susceptibilitity apparatus,” Journal of Chemical Society, pp. 4190–4191, 1958. View at: Publisher Site | Google Scholar
25. M. Joseph, A. Sreekanth, V. Suni, and M. R. P. Kurup, “Spectral characterization of iron(III) complexes of 2-benzoylpyridine $N\left(4\right)$-substituted thiosemicarbazones,” Spectrochimica Acta Part A, vol. 64, no. 3, pp. 637–641, 2006. View at: Publisher Site | Google Scholar
26. K. P. Deepa and K. K. Aravindakshan, “Synthesis, characterization and thermal studies of thiosemicarbazones of N-methyl- and N-ethylacetoacetanilide,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 30, no. 8, pp. 1601–1616, 2000. View at: Google Scholar
27. S. Chandra and L. K. Gupta, “EPR, mass, IR, electronic, and magnetic studies on copper(II) complexes of semicarbazones and thiosemicarbazones,” Spectrochimica Acta Part A, vol. 61, no. 1-2, pp. 269–275, 2005. View at: Publisher Site | Google Scholar
28. N. S. Youssef and K. H. Hegab, “Thiosemicarbazones derives from 2-acetylpyrrole and 2-acetylfuran,” Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, vol. 35, no. 5, pp. 391–399, 2005. View at: Publisher Site | Google Scholar
29. S. Chandra, U. Kumar, and H. S. Verma, “Cobalt(II) complexes of semicarbazones and thiosemicarbazones,” Journal of Saudi Chemical Society, vol. 7, no. 3, pp. 337–346, 2003. View at: Google Scholar
30. N. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, John Wiley & Sons, New York, NY, USA, 3rd edition, 1978.
31. R. A. Bailey, S. L. Kozak, T. W. Michelson, and W. N. Mills, “Infrared spectra of complexes of the thio ions,” Coordination Chemistry Reviews, vol. 6, no. 4, pp. 407–445, 1971. View at: Publisher Site | Google Scholar
32. R. E. Hester and W. E. L. Grossman, “Vibrational analysis of bidentate nitrate and carbonate complexes,” Inorganic Chemistry, vol. 5, no. 8, pp. 1308–1312, 1966. View at: Publisher Site | Google Scholar
33. S. Chandra and U. Kumar, “Studies on the synthesis, stereochemistry and antifungal properties of coumarin thiosemicarbazone and its Ni(II) and Cu(II) complexes,” Journal of Saudi Chemical Society, vol. 8, no. 1, pp. 77–84, 2004. View at: Google Scholar
34. A. B. P. Lever, “Electronic spectra of ${\text{d}}^{\text{n}}$ ions,” in Inorganic Electronic Spectroscopy, pp. 376–611, Elsevier, Amsterdam, The Netherlands, 2nd edition, 1984. View at: Google Scholar
35. S. Chandra and A. Kumar, “Spectral studies on Co(II), Ni(II) and Cu(II) complexes with thiosemicarbazone (${\text{L}}^1$) and semicarbazone (${\text{L}}^2$) derived from 2-acetyl furan,” Spectrochimica Acta Part A, vol. 66, no. 4-5, pp. 1347–1351, 2007. View at: Publisher Site | Google Scholar
36. S. Chandra and U. Kumar, “Spectral and magnetic studies on manganese(II), cobalt(II) and nickel(II) complexes with Schiff bases,” Spectrochimica Acta Part A, vol. 61, no. 1-2, pp. 219–224, 2005. View at: Publisher Site | Google Scholar
37. S. Chandra and U. Kumar, “Spectroscopic characterization of copper(II) complexes of indoxyl $N\left(4\right)$-methyl thiosemicarbazone,” Spectrochimica Acta Part A, vol. 60, no. 12, pp. 2825–2829, 2004. View at: Publisher Site | Google Scholar
38. B. J. Hathaway, J. N. Bardley, and R. D. Gillard, Eds., Essays in Chemistry, Academic Press, New York, NY, USA, 1971.
39. S. K. Sengupta, O. P. Pandey, B. K. Srivastava, and V. K. Sharma, “Synthesis, structural and biochemical aspects of titanocene and zirconocene chelates of acetylferrocenyl thiosemicarbazones,” Transition Metal Chemistry, vol. 23, no. 4, pp. 349–353, 1998. View at: Publisher Site | Google Scholar
40. Z. H. A. El-Wahab, M. M. Mashaly, A. A. Salman, B. A. El-Shetary, and A. A. Faheim, “Co(II), Ce(III) and ${\text{UO}}_2$(VI) bis-salicylatothiosemicarbazide complexes: binary and ternary complexes, thermal studies and antimicrobial activity,” Spectrochimica Acta Part A, vol. 60, no. 12, pp. 2861–2873, 2004. View at: Publisher Site | Google Scholar

Copyright

Copyright © 2007 Sulekh Chandra et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.