Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Electronic, e.p.r., cyclic voltammetric and biological activities of copper(II) complexes with macrocyclic ligands

  • 204 Accesses

  • 29 Citations

Abstract

Eight new macrocyclic ligands have been prepared by the reaction of the precursor diketone (benzil, glyoxal, diacetyl or 2,3-pentanedione) with a diamine (thiosemicarbazide or semicarbazide). Copper(II) complexes of these ligands have been synthesized and characterized by elemental analysis, molar conductance, magnetic susceptibility, i.r., u.v.–vis, 1H-n.m.r., mass and e.p.r. spectral studies. Mass, n.m.r. and i.r. data indicate the condensation of the diamine and diketone and the whole molecular ion structure. g-Values are calculated for all of the complexes in polycrystalline form as well as in DMSO solution. Spin Hamiltonian values and bonding parameters have also been calculated which indicates that an unpaired electron is present in the \({d_{x^2-y^2}}\) orbital. The metal-ligand bonding parameters shows strong in-plane σ sigma and in-plane π bonding. The magnetic and spectral data indicate tetragonal geometry for all of the complexes except [CuH2L4]Cl2 and [CuH2L4]Cl2 which are square planar. From c.v. data reversible CuII/CuI couples are observed for these complexes. The macrocyclic complexes show more antibacterial and antiviral activity as compared to the ligands. The antibacterial activities of the compounds were tested against S. aureus, S. subtillis and E. coli.

This is a preview of subscription content, log in to check access.

References

  1. O.D. Fox, M.G.B. Drew, E.J.S. Wilkinson and P.O. Beer, Chem. Commun., 319 (2000).

  2. E. Labisbal A. Sousa A. Castineiras A. Gracia-Vazquez J. Romero D.X. West (2000) Polyhedron 19 1255 Occurrence Handle10.1016/S0277-5387(00)00383-1

  3. M. Canadas E. Lopez-Torres A.M. Arias M.A. Mendiola M.T. Sevilla (2000) Polyhedron 19 2059 Occurrence Handle10.1016/S0277-5387(00)00505-2

  4. D.X. West E. Liberia S.B. Padhye R.C. Chikate P.B. Sonawane A.S. Kumbar R.S. Yeranda (1993) Coord. Chem. Rev. 123 49 Occurrence Handle10.1016/0010-8545(93)85052-6

  5. C.M. Liu G. Xiong X.Z. You YJ. Liu (1996) Polyhedron 15 4565 Occurrence Handle10.1016/0277-5387(96)00163-5

  6. R.F. Keyes J.J. Carter E.E. Englund M.M. Daly G.G. Stone A.M. Nilius Z. Ma (2003) J. Med. Chem. 46 1795 Occurrence Handle10.1021/jm025580k Occurrence Handle12723941

  7. A.A. Isse, A. Gennaro and E. Vianello, J. Chem. Soc., Dalton Trans., 2091 (1993).

  8. S. Chandra Sangeetika (2004) Spectro chim. Acta A 60 147

  9. S.B. Padhye G.B. Kauffinan (1985) Coord. Chem. Rev. 63 127 Occurrence Handle10.1016/0010-8545(85)80022-9

  10. S. Chandra Sangeetika (2002) Indian J. Chem. Section A 41 1629

  11. S. Chandra Sangeetika A. Rathi (2001) J. Saudi Chem. Soc. 5 175

  12. B.J. Hathaway A.A.G. Tomlinson (1970) Coord. Chem. Rev. 5 1 Occurrence Handle10.1016/S0010-8545(00)80073-9

  13. A.B.P. Lever (1968) Inorganic Electronic Spectroscopy Elsevier Publishing Company Amsterdam, London NY 328

  14. B.J. Hathaway D.E. Billing (1970) Coord. Chem. Rev. 5 143 Occurrence Handle10.1016/S0010-8545(00)80135-6

  15. M.L. Kantouri M. Hartophylles (1992) Polyhedron 11 789 Occurrence Handle10.1016/S0277-5387(00)86011-8

  16. B.J. Hathaway, Essays in Chemistry in J.N. Bardley and R.D. Gillard (Eds), Academic Press, New York, 1971, p. 61.

  17. B.J. Hathaway, R.J. Dudely and P. Nichollas, J. Chem. Soc., 1845 (1968).

  18. M. Baldini M.B. Ferrari F. Bisceglie G. Pelosi S. Pinelli P. Tarasconi (2003) Inorg. Chem. 42 2049 Occurrence Handle10.1021/ic026131d Occurrence Handle12639140

  19. D.X. West H. Gebremedhin T.J. Romack (1994) Transition Met. Chem. 19 426

  20. M.P. Donzello D. Dini G.D. Arcangelo C. Ercolani R. Zhan Z. Qu P.A. Stuzhin K.M. Kadish (2003) J. Am. Chem. Soc. 125 14190 Occurrence Handle10.1021/ja0344361 Occurrence Handle14611258

  21. T.D. Thangadurai K. Natarajan (2001) Transition Met. Chem. 26 717 Occurrence Handle10.1023/A:1012081112872

Download references

Author information

Correspondence to Sulekh Chandra.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Chandra, S., Sangeetika & Thakur, S. Electronic, e.p.r., cyclic voltammetric and biological activities of copper(II) complexes with macrocyclic ligands. Transition Met Chem 29, 925–935 (2004). https://doi.org/10.1007/s11243-004-3224-7

Download citation

Keywords

  • Antibacterial Activity
  • Magnetic Susceptibility
  • Diamine
  • Antiviral Activity
  • Unpaired Electron