Skip to main content
SpringerLink
Log in

Synthesis, characterization and ascorbic acid oxidase mimetic catalytic activity of copper(II) picolyl hydrazone complexes

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

Four new picolyl hydrazones were prepared via Schiff-base condensation of picolonic acid hydrazide with α-formyl-(L1), α-acetyl-(L2), α-benzoyl-(L3) pyridine and α-formyl-(L4) thiophene. Copper(II) complexes of these hydrazones and a series of copper(II) complexes containing (L2) and various anions (Cl, Br, NO3, SCN, SO4, ClO4, AcO, PF6 and BF4) have been synthesized. Elemental, thermal analysis, molar conductivity, magnetic moment measurements and spectral (i.r., electronic and e.s.r.) studies have been used to characterize the prepared compounds. The overall structure and reactivity of the reported copper(II) chelates critically depend on the ligand structure and the nature of counter anion incorporated in the complex molecule. Octahedral [complex (7)], square-pyramidal [complex (8)] and square-planar monomeric species [complexes (1–6), (9) and (10)] and a dimeric structure with oxygen bridge in square-planar geometry [complexes (11) and (12)] were suggested. The reported copper(II) complexes exhibit promising oxidase catalytic activity towards the aerobic oxidation of vitamin C. A linear correlation exists between the oxidase catalytic activity and the Lewis-acidity of the central copper(II) ion created by the donating properties of the parent ligand, as well the irregularity of the coordination environment. The probable mechanistic implications of the catalytic oxidation reactions are discussed.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. T. Bugg (1997) An Introduction to Enzyme and Coenzyme Chemistry, Ch. 3 EditionNumber1 Black Well Science Oxford

    Google Scholar 

  2. W. Kaim B. Schwederski (1995) Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life Wiley New York

    Google Scholar 

  3. J. Reedijk (1993) Bioinorganic Catalysis Marcel Dekker New York

    Google Scholar 

  4. A. Messer Schmidt R. Huber (1990) Eur. J. Biochem. 187 341 Occurrence Handle10.1111/j.1432-1033.1990.tb15311.x Occurrence Handle1:CAS:528:DyaK3cXhtFCrsbY%3D Occurrence Handle2404764

    Article  CAS  PubMed  Google Scholar 

  5. DE. Fenton (1995) Biocoordination Chemistry Oxford University Press Oxford 1–33

    Google Scholar 

  6. L.I. Ingraham DL. Meyer (1985) Biochemistry of Dioxygen EditionNumber4 Plenum New York

    Google Scholar 

  7. JS. Valentine CS. Foote A. Greenberg JF. Libman (1994) Active Oxygen in Biochemistry, Chap. 4 EditionNumber1 Chapman & Hall New York

    Google Scholar 

  8. A. Messerschmidt H. Luecke R. Huber (1993) J. Mol. Biol. 230 997 Occurrence Handle10.1006/jmbi.1993.1215 Occurrence Handle1:CAS:528:DyaK3sXisFSlt7w%3D Occurrence Handle8478945

    Article  CAS  PubMed  Google Scholar 

  9. Latour JM. (1988). Bull. Soc. Chim. Fr. 508

  10. R. Jorge K. Bernt (1997) J. Chem. Soc. Dalton Trans. 20 3793

    Google Scholar 

  11. S. Olivier C. Morgan D. Benedict G. Michel R. Eric J. Yves Y. Le R. Oli (2002) Eur J. Inorg. Chem. 8 2007

    Google Scholar 

  12. A. Jens M. Franc K. Elisabeth P. Hans (2002) Chem. Europ. J. 8 IssueID1 247 Occurrence Handle10.1002/1521-3765(20020104)8:1<247::AID-CHEM247>3.0.CO;2-P

    Article  Google Scholar 

  13. G. Debjani S. Atindro B. Rupendranath D. Amitava (2002) J. Chem. Soc. Dalton Trans. 6 1220

    Google Scholar 

  14. R. Pattubala N. Munirthinam C. Akhil (2003) Eur. J. Inorg. Chem. 12 2318

    Google Scholar 

  15. KB. Santra A.NP. Reddy M. Nethaji RA. Chkravarty (2001) J. Chem. Soc. Dalton Trans. 24 3553 Occurrence Handle10.1039/b109332k

    Article  Google Scholar 

  16. D.R. Makote C. Chattejee (1999) Indian J. Chem. Sect. A 38 IssueID8 783

    Google Scholar 

  17. A.M. Ramadan I.M. El-Mehasseb (1998) Transition Met. Chem. 23 183 Occurrence Handle10.1023/A:1006959513023

    Article  Google Scholar 

  18. A. Latif Abuhijleh and Wood C., J. Inorg. Biochem. , 64 , 55 (1996); Inorg. Chim Acta , 209 , 187 (1992); 215 , 131 (1993); Polyhedron , 15 , 285 (1996); Y.Y. Lim and Tan E., J. Mol. Catal. , 85 , 173 (1993); F.␣Zippel Ahlers F., Werner R., Hanes W., H. Friedrich and Krebs B., Inorg. Chem. , 35 , 3409 (1986)

  19. G. Struve (1896) J. Prakt. Chem. 52 170

    Google Scholar 

  20. RJ. Henry (1974) Clinical Chemistry, Principles and Techniques EditionNumber2 Churchill Livingstones New York 1393–1397

    Google Scholar 

  21. RM. Silverstein G.C. Bassler TC. Morrill (1981) Spectrometric Identification Of Organic Compounds EditionNumber4 Wiley New York

    Google Scholar 

  22. Z. Gang M. Yongxiang (1991) Polyhedron. 10 2185 Occurrence Handle10.1016/S0277-5387(00)86139-2 Occurrence Handle1:CAS:528:DyaK38XnsVymtA%3D%3D

    Article  CAS  Google Scholar 

  23. B.S. Gang L. Kapur (1990) Inorg. Chim. Acta. 170 171 Occurrence Handle10.1016/S0020-1693(00)80472-7

    Article  Google Scholar 

  24. S. Goel O.P. Pandley SK. Singupta (1991) Synth. React. Inorg. Met.-Org.Chem. 21 1001 Occurrence Handle1:CAS:528:DyaK3MXms12iu74%3D

    CAS  Google Scholar 

  25. Ismail KZ., Transition Met. Chem. , 22 , 565 (1997); Z. Gang and Yuan C., Transition Met. Chem. , 19 , 218 (1994)

  26. J.J. Lopaez-Carriga G.T. Babcock JF. Harrison (1986) J. Am. Chem. Soc. 108 7241 Occurrence Handle10.1021/ja00283a019

    Article  Google Scholar 

  27. R.J.H. Clark CS. Williams (1965) Inorg. Chem. 4 350 Occurrence Handle10.1021/ic50025a020 Occurrence Handle1:CAS:528:DyaF2MXkvVWisA%3D%3D

    Article  CAS  Google Scholar 

  28. K. Nakamoto (1986) Infrared and Raman Spectra of Inorganic and Coordination Compounds Wiley New York

    Google Scholar 

  29. DA. Waldwin A.B.P. Lever RV. Parish (1971) Inorg. Chem. 10 107

    Google Scholar 

  30. JR. Ferraro (1971) Low Frequency Vibrations of Inorganic and Coordination Compounds Plenum New York

    Google Scholar 

  31. Calderazo F., Floriani C., R. Henzi and Leplattenier F., J. Chem. Soc. , (A) 1378 (1969); M. Gerloch and Mabbs FE., J. Chem. Soc. , (A), 1900 (1967); A. Ramadan M., I.M. El-Mehasseb and Issa RM., Transition Met. Chem. , 22 , 529 (1997); F.A. Cotton and Wilkinson G., Advanced Inorganic Chemistry , 5th edit., Wiley, New York, 1988

  32. DX. West JS. Ives J. Krejci MM. Salberg TL. Zumahlen G.A. Bain AE. Liberta (1995) Polyhedron. 14 2189 Occurrence Handle10.1016/0277-5387(95)00010-P Occurrence Handle1:CAS:528:DyaK2MXnslWnsbw%3D

    Article  CAS  Google Scholar 

  33. West DX., Nassar AA., F.A. El-Saied and Ayad MI., Transition Met. Chem. , 23 , 321 (1998); 23 , 423 (1998); West DX., Huffman DL., J.S. Saleda and Liberta AE., Transition Met. Chem. , 16 , 565(1991); West DX., I. Thientaravanich and Liberta AE., Transition Met. Chem. , 20 , 303 (1995)

  34. S. Gourbatsis S.P. Perlepes N. Hadjilidis (1990) Transition Met. Chem. 15 300 Occurrence Handle10.1007/BF01061939 Occurrence Handle1:CAS:528:DyaK3cXlsVCitrg%3D

    Article  CAS  Google Scholar 

  35. K. Nakamoto PJ. McCarthy (1968) Spectroscopy and Structure of Metal Chelate Compounds Wiley New York

    Google Scholar 

  36. A.BP. Lever (1970) Inorganic Electronic Spectroscopy Elsevier Amsterdam

    Google Scholar 

  37. Ramadan A.M., El-Naggar M.M. J. Inorg. Biochem. , 63 , 143 (1996); Ramadan AM., J. Inorg. Biochem. , 65 , 183 (1997)

  38. A.B.P. Lever E. Mantovani (1971) Inorg. Chem. 10 817 Occurrence Handle10.1021/ic50098a031 Occurrence Handle1:CAS:528:DyaE3MXhtFOksbg%3D

    Article  CAS  Google Scholar 

  39. B.J. Hathaway OE. Billing (1970) Coord. Chem. Rev. 5 143 Occurrence Handle10.1016/S0010-8545(00)80135-6 Occurrence Handle1:CAS:528:DyaE3cXkvFCitbw%3D

    Article  CAS  Google Scholar 

  40. Procter IM., Hathaway B.J., Nicholls P. (1969). J. Chem. Soc., (A). 1678

  41. N.D. Kulkarrni PK. Bhattcharya (1989) Transition Met. Chem. 14 303 Occurrence Handle10.1007/BF01098235

    Article  Google Scholar 

  42. Maajan M., K.N. Saxena and Saxena CP., J. Inorg. Nucl. Chem. , 43 , 2148 (1981); Einstein JC., J. Chem. Phys. , 28 , 323 (1958); K.K. Sharma and Chandra S., Transition Met. Chem. , 9 , 401 (1984)

  43. J.F. Villa WE. Hatfield (1972) Inorg. Chem. 11 1331 Occurrence Handle10.1021/ic50112a035 Occurrence Handle1:CAS:528:DyaE38Xkt1Kns7g%3D

    Article  CAS  Google Scholar 

  44. L. Antolini L. Menabue M. Saladini (1985) Inorg. Chem. 24 1219 Occurrence Handle1:CAS:528:DyaL2MXhsVaitb0%3D

    CAS  Google Scholar 

  45. Hathaway BJ., Essays in Chemistry , Academic Press, New York, 1971; M.F. El-Shazly, A. El-Dissoky, T.M. Salem and Osman MM., Inorg. Chim. Acta , 40 , 1 (1980)

  46. Hudson A., J. Mol. Phys. , 10, 575 (1966); Bersuker IB., Coord. Chem. Rev. , 14 , 357 (1975)

  47. A. El-Dissoky LS. Refaat (1984) Inorg. Chim Acta. 87 213 Occurrence Handle10.1016/S0020-1693(00)81839-3

    Article  Google Scholar 

  48. D. Kivelson R. Neiman (1961) J. Chem. Phys. 35 149 Occurrence Handle1:CAS:528:DyaF3MXhtlGntbc%3D

    CAS  Google Scholar 

  49. KD. Karlin Y. Gultneh T. Nicholson J. Zubieta (1985) Inorg. Chem. 24 3725 Occurrence Handle1:CAS:528:DyaL2MXlvVynsbc%3D

    CAS  Google Scholar 

  50. Bulla J., T. Kiss and Janeson RF., Inorg. Chem. , 31 , 58 (1992); Speier G., J. Mol. Catal. , 37 , 259 (1986); Demmin TR., M.D. Swerdloff and Rogic MM., J. Am. Chem. Soc. , 103 , 5795 (1981)

  51. D. Cox L. Que (1988) J. Am. Chem. Soc. 110 8085 Occurrence Handle1:CAS:528:DyaL1MXitVChug%3D%3D

    CAS  Google Scholar 

  52. Williams R.J.P. (1986). Metallo-Enzyme Catalysis: The Entatic State, J. Mol. Catal.-Rev. Issue, 1

  53. B.L. Vallee R.JP. illiams (1968) Proc. Natl. Acad. Sci. USA. 59 498 Occurrence Handle1:CAS:528:DyaF1cXhtFWmurw%3D Occurrence Handle5238980

    CAS  PubMed  Google Scholar 

  54. G.H. Olive S. Olive (1977) Coordination and Catalysis EditionNumber1 Verlag Chemie Weinheim, New York

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Education, Tanta University, Kafr El-Sheikh, Egypt

    Abd El-Motaleb & M. Ramadan

  2. Department of Chemistry, Faculty of Science, Tanta University, Egypt

    Raafat M. Issa

Authors
  1. Abd El-Motaleb
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Ramadan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Raafat M. Issa
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

El-Motaleb, A., Ramadan, M. & Issa, R.M. Synthesis, characterization and ascorbic acid oxidase mimetic catalytic activity of copper(II) picolyl hydrazone complexes. Transition Met Chem 30, 471–480 (2005). https://doi.org/10.1007/s11243-005-0414-x

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-005-0414-x

Keywords

Search

Navigation