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BioMetals

, Volume 21, Issue 4, pp 491–501 | Cite as

Synthesis, characterization of some transition metal(II) complexes of acetone p-amino acetophenone salicyloyl hydrazone and their anti microbial activity

  • Vinod P. Singh
  • Anshu Katiyar
  • Shweta Singh
Article

Abstract

Complexes of the type [M(apash)Cl] and [M(Hapash)(H2O)SO4], where M = Mn(II), Co(II), Ni(II), Cu(II) and Zn(II); Hapash = acetone p-amino acetophenone salicyloyl hydrazone have been synthesized and characterized by elemental analyses, molar conductance, magnetic moments, electronic, ESR and IR spectra, thermal studies (TGA & DTA) and X-ray diffraction studies. The ligand coordinates through two >C=N and a deprotonated enolate group in all the chloro complexes, whereas through two >C=N– and a >C=O group in all the sulfato complexes. The electronic spectra suggest a square planar geometry for Co(II), Ni(II) and Cu(II) chloride complexes and an octahedral geometry for the sulfate complexes. ESR data show an isotropic symmetry for [Cu(apash)Cl] and [Cu(Hapash)(H2O)SO4] in solid state. However, ESR spectra of both Cu(II) complexes indicate the presence of unpaired electron in \( {\text{d}}_{{{\text{x}}^{2} - {\text{y}}^{2} }}. \)The X-ray diffraction parameters for [Co(apash)Cl] and [Cu(Hapash)(H2O)SO4] complexes correspond to a tetragonal and an orthorhombic crystal lattices, respectively. Thermal studies of [Co(apash)Cl] complex shows a multi-step decomposition pattern. Most of the complexes show better antifungal activity than the standard miconazole against a number of pathogenic fungi. The antibacterial activity of these complexes has been evaluated against E. coli and Clostridium sp. which shows a moderate activity.

Keywords

Metal(II) complexes Synthesis and characterization Salicyloyl hydrazone Antifungal Antibacterial activity 

Notes

Acknowledgements

The authors thank the Head, Department of Chemistry, Indian Institute of Technology, Kanpur for recording UV-Vis, IR and ESR spectra, Dr. Nand Lal, Department of Life Sciences, C. S. J. M. University, Kanpur for help in biological screening.

References

  1. Abd El-Wahab ZH, El-Sarrag MR (2004) Derivatives of phosphate Schiff base transition metal complexes: synthesis, studies and biological activity. Spectrochim Acta 60A:271–277Google Scholar
  2. Bhattacharya S, Mandal SS (1996) DNA cleavage by intercalatable cobalt-bis picolylamine complexes activated by visible light. Chem Commun 1515–1516Google Scholar
  3. Bigoli F, Cassoux P, Deplano P, Mercuri ML, Pellinghelli MA, Pintus G, Serpe A, Trogu EF (2000) Synthesis, structure and properties of new unsymmetrical nickel dithiolene complexes useful as near-infrared dyes. J Chem Soc Dalton Trans 24:4639–4644CrossRefGoogle Scholar
  4. Bindu P, Kurup MRP, Satyakeerty TR (1999) EPR, cyclic voltametric and biological activities of copper(II) complexes of salicylaldehyde N(4)-substituted thiosemicarbazone and heterocyclic bases. Polyhedron 18:321–331CrossRefGoogle Scholar
  5. Butcher RJ, Jasinski J, Mockler GM, Sinn E (1976) Synthesis and crystal structure of bis-MU-(5-chloro 2-hydroxy N-methyl alpha-phenyl benzylideneiminato-N,O)-bis[ethanol (nitrato-O-O’) nickel(II)] New type of nickel(II) dimmer. J Chem Soc Dalton Trans 1099–1102Google Scholar
  6. Chapman SK (1991) Perspectives on bioinorganic chemistry, vol I. JAI PressGoogle Scholar
  7. Chohan ZH, Farooq MA, Scozzafava A, Supuran CT (2002) Antibacterial Schiff bases of oxalyl-hydrazine/diamide incorporating pyrolyl and salicylyl moieties and of their zinc(II) complexes. J Enz Inh Med Chem 17:1CrossRefGoogle Scholar
  8. Cotton FA, Wilkinson G, Murillo CA, Bochmann M (2003) Advanced inorganic chemistry, 6th edn. Wiley, New YorkGoogle Scholar
  9. Deepa K, Aravindakshan KK (2005) Synthesis, characterization and antifungal studies of metal complexes of benzoyl- and salicylylhydrazones of omega-bromoacetanilide. Synth React Inorg Met-Org Nano-Met Chem 35:409–416CrossRefGoogle Scholar
  10. Dutta RL, Syamal A (1993) Elements of magnetochemistry, 2nd edn. Affiliated East-West Press Pvt. Ltd., New DelhiGoogle Scholar
  11. Geary WJ (1971) The use of conductivity measurements in organic solvents for the characterization of coordination compounds. Coord Chem Rev 7:81CrossRefGoogle Scholar
  12. Greenwood NN, Earnshaw A (1998) Chemistry of the elements. Butterworth-Heinmann, OxfordGoogle Scholar
  13. Hathaway BJ, Billing DE (1970) Electronic properties and stereochemistry of mono-nuclear complexes of copper(II) ion. Coord Chem Rev 5:143CrossRefGoogle Scholar
  14. Johari RB, Sharma RC (1988) Synthetic and biocidal studies of some bivalent metal complexes of benzaldehyde salicyloylhydrazone. J Indian Chem Soc 65:793–794Google Scholar
  15. Karlin KD, Tyeklar Z (1993) Bioinorganic chemistry of copper. Chapman and Hall, New YorkGoogle Scholar
  16. Kumar M, Qiu D, Spiro TG, Ragsdale SW (1995) A methylnickel intermediate in a bimetallic mechanism of acetyl-coenzyme-A synthesis by anaerobic bacteria. Science 270:628–630PubMedCrossRefGoogle Scholar
  17. Kyritsis P, Dennison C, Kalverda AP, Canters GW, Sykes AG (1994) Redox reactivity of the type-1 (blue) copper protein amicyanine from thiobacillus versutus with inorganic complexes. J Chem Soc Dalton Trans 3017–3023Google Scholar
  18. Lever ABP (1984) Inorganic electronic spectroscopy, 2nd edn. Elsevier, AmsterdamGoogle Scholar
  19. Macke HR, Williams AF (1988) Photoinduced electron transfer. Elsevier, Amsterdam, p. 28Google Scholar
  20. Mills CF (1989) Zinc in human biology. Springer–Verlag, New YorkGoogle Scholar
  21. Nagar R (1990) Synthesis, characterization and microbial activity of some transition metal complexes involving potentially active O-donor and N-donor heterocyclic ligands. J Inorg Biochem 40:349–356PubMedCrossRefGoogle Scholar
  22. Nakamoto K (1997) Infrared and Raman spectra of inorganic and coordination compounds. Wiley Interscience, New YorkGoogle Scholar
  23. Narang KK, Singh VP (1993) Synthesis and characterization of cobalt(II), nickel(II), copper(II) and zinc(II) complexes with acetylacetone bis-benzoyl hydrazone and acetylacetone bis-isonicotinoyl hydrazone. Transit Met Chem 18:287–290Google Scholar
  24. Narang KK, Singh VP (1996) ESR studies on acylhydrazine and hydrazone copper(II) sulfate complexes. Transit Met Chem 21:507–511Google Scholar
  25. Narang KK, Pandey JP, Singh VP (1994) Synthesis, characterization and physicochemical studies of some copper(II) tetrathiocynato dithallate(I) complexes with hydrazides and hydrazones. Polyhedron 13:529–538CrossRefGoogle Scholar
  26. Nishida Y, Kida S (1979) Splitting of d-orbitals in square planar complexes of copper(II), nickel(II) and cobalt(II). Coord Chem Rev 27:275–298CrossRefGoogle Scholar
  27. Panchal PK, Parekh HM, Patel MN (2005) Preparation, characterization and toxic activity of oxovanadium(IV) mixed-ligand complexes. Toxicol Environ Chem 87:313CrossRefGoogle Scholar
  28. Shama SA, Omara H (2001) Synthesis and characterization of some transition metal complexes with Shiff bases derived from 2-hydroxy acetylacetophenone. Spectrosc Lett 34:49CrossRefGoogle Scholar
  29. Singh VP, Gupta P (2006) Synthesis, characterization and biocidal activities of some metal(II) complexes with diacetyl salicylaldehyde acyldihydrazone. J Coord Chem 59:1483–1494CrossRefGoogle Scholar
  30. Singh OI, Damayanti M, Singh NR, Singh RKH, Mohapatra M, Kadam RM (2005) Synthesis, EPR and biological activities of bis(1-n-butyl amidino-o-alkylurea) copper(II) chloride complexes. Polyhedron 24:909–916CrossRefGoogle Scholar
  31. Thimmaiah KN, Chandrappa GT, Rangaswamy, Jayarama (1984) Structural studies of biologically active complexes of zinc(II), cadmium(II), mercury(II) and copper(II) with p-anisaldehyde thiosemicarbazone. Polyhedron 3:1237–1239CrossRefGoogle Scholar
  32. Vogel AI (1989) Vogel’s text book of quantitative chemical analysis, 5th edn. Longman, AmsterdamGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC. 2008

Authors and Affiliations

  1. 1.Chemistry Department, Faculty of ScienceBanaras Hindu UniversityVaranasiIndia

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