Skip to main content
SpringerLink
Log in

Synthesis, characterization, spectroscopic and catalytic oxidation studies of Fe(III), Ni(II), Co(III), V(IV) and U(VI) Schiff base complexes with N, O donor ligands derived from 2,3-diaminopyridine

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Fifteen new complexes of transition metals were designed using three Schiff base ligands and aldol condensation of 2,3-diaminopyridine with 5-R-2-hydroxybenzaldehyde (R = F, Cl, Br) in the 1:2 molar ratio. The tetradentate ligands N,N′-bis(5-R-2-hydroxybenzaldehyde) pyridine were acquired with the common formula H2[(5-R-sal)2py] and characterized by IR, UV–Vis spectra, 1H-NMR and elemental analysis. These ligands produce 1:1 complexes M[(5-R-sal)2py] with Fe(III), Ni(II), Co(III), V(IV) and U(VI) metal ions. The electronic property and nature of complexes were identified by IR, UV–Vis spectra, elemental analysis, X-ray crystallography and cyclic voltammetric methods. The catalytic activity of complexes for epoxidation of styrene with UHP as primary oxidant at minimal temperature (10 °C) has been planned. The spectral data of the ligands and their complexes are deliberate in connection with the structural changes which happen due to complex preparation. The electrochemical outcome has good conformability with what suggested for electronic interaction among metal center and ligand by the UV–Vis and IR measurements.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 2
Fig. 8

Similar content being viewed by others

References

  1. P.A. Vigato, S. Tamburini, Coor. Chem. Rev. 248, 1717 (2004)

    Article  CAS  Google Scholar 

  2. A.H. Kianfar, M. Kazemi Boudani, M. Roushani, M. Shamsipur, J. Iran. Chem. Soc. 9, 449 (2012)

    Article  CAS  Google Scholar 

  3. N.E. Borisova, M.D. Reshetova, Y.A. Ustynyuk, Chem. Rev. 107, 46 (2007)

    Article  CAS  Google Scholar 

  4. D.M. Boghaei, S. Mohebi, Tetrahedron 58, 5357 (2002)

    Article  CAS  Google Scholar 

  5. S. Mohebi, D.M. Boghaei, A.H. Sarvestani, Appl Catal A: Gen 278, 263 (2005)

    Article  Google Scholar 

  6. S. Mohebbi, S. Raiati, F. Nikpour, J. Mol. Catal. A: Chem. 256, 265 (2006)

    Article  CAS  Google Scholar 

  7. S. Mohebbi, A. Hossein Sarvestani, Trans. Met. Chem. 31, 749 (2006)

    Article  CAS  Google Scholar 

  8. D.E. Hamilton, R.S. Drago, A. Zombeck, J. Am. Chem. Soc. 109, 374 (1987)

    Article  CAS  Google Scholar 

  9. Z. Asadi, M. Asadi, F. Dehghani Firuzabadi, R. Yousefi, M. Jamshidi, J. Iran. Chem. Soc. 11, 423 (2014)

    Article  CAS  Google Scholar 

  10. Z. Xinde, W. Chenggang, L. Zhiping, L. Zhefeng, W. Zishen, Synth React Inorg Met Org Chem 26, 955 (1996)

    Article  Google Scholar 

  11. L.G. Marzilli, P.A. Marzilli, J. Halpern, J. Am. Chem. Soc. 93, 1374 (1971)

    Article  Google Scholar 

  12. K. Mitra, S. Biswas, C. Robert Lucas, Inorg. Chim. Acta 359, 1997 (2006)

    Article  CAS  Google Scholar 

  13. A.A. Adel, A. Emara Azza, A. Abou Hussen, Spectro Chim Acta Part A 64, 1010 (2006)

    Article  Google Scholar 

  14. D.M. Boghaei, S. Mohebi, J. Mol. Catal. A: Chem. 179, 41 (2002)

    Article  CAS  Google Scholar 

  15. S. Mohebi, D.M. Boghaei, Synth. React. Inorg. Met. Org. Chem 34, 611 (2004)

    Article  CAS  Google Scholar 

  16. S. Sarawat, G.S. Srivastava, R.G. Mehrotra, J. Organomet. Chem. 129, 155 (1977)

    Article  Google Scholar 

  17. J.R. Ferraro, Low Frequency Vibrations of Inorganic and Coordination Compounds, 1st edn. (Plenum Press, New York, 1971), p. 168

    Google Scholar 

  18. E. Pretsch, J. Seibl, Tables of Spectral Data for Structure Determination of Organic Compounds (Springer-Verlag, Berlin, 1983)

    Book  Google Scholar 

  19. G. Venkatachalam, R. Ramesh, Inorg. Chem. Commun. 9, 703 (2006)

    Article  CAS  Google Scholar 

  20. S. Kannan, R. Ramesh, Polyhedron 25, 3095 (2006)

    Article  CAS  Google Scholar 

  21. S.A. Abdel-latif, H.B. Hassib, Y.M. Issa, Spectrochim. Acta, Part A 67, 950–957 (2007)

    Article  CAS  Google Scholar 

  22. M. El-Behery, H. El-twigry, Spectrochim. Acta, Part A 67, 28 (2007)

    Article  Google Scholar 

  23. P. Noblia, M. Vieites, M.H. Torre, J. Inorg. Biochem. 100, 281 (2006)

    Article  CAS  Google Scholar 

  24. A.A. Soliman, S.A. Ali, Spectrochimica Acta part A 65, 841 (2006)

    Article  Google Scholar 

  25. A. Fuerte, M. Iglesias, F. Sanchez, J. Mol. Cat. A: Chem. 211, 227 (2004)

    Article  CAS  Google Scholar 

  26. N.S. Biradar, V.H. Kulkami, J. Inorg. Nucl. Chem. 33, 3781 (1971)

    Article  CAS  Google Scholar 

  27. Proc. Indian Acad. Sci. (Chem. Sci.) 115, 91 (2003)

  28. R. Ramesh, S. Maheswaran, J. Inorg. Biochem. 96, 457 (2003)

    Article  CAS  Google Scholar 

  29. W.A. Nugent, J.M. Meyer, Metal–Ligand Multiple Bonds (Wiley, New York, 1988)

    Google Scholar 

  30. H.H. Jaffe, Chem. Rev. 53, 191 (1953)

    Article  CAS  Google Scholar 

  31. N.S. Venkataramanan, S. Premsingh, S. Rajagopal, K. Pitchumani, J. Org. Chem. 68, 7460 (2003)

    Article  CAS  Google Scholar 

  32. SMART version 5.630 and SAINT-plus version 6.45 (Bruker-Nonius Analytical X-ray Systems Inc, Madison, WI, USA, 2003)

  33. G.M. Sheldrick, SADABS, Program for Area Detector Absorption Correction (University of Göttingen, Göttingen, 1997)

  34. C. Coperet, H. Adolfson, K.B. Sharpless, Chem. Commun. 16, 1565 (1997)

    Article  Google Scholar 

  35. D.E. de Vos, B.F. Sels, M. Reynaers, Y.V.S. Rao, P.A. Jacobsen, Tetrahedron Lett. 39, 3221 (1998)

    Article  Google Scholar 

  36. M.G. Finn, K.B. Sharpless, J. Am. Chem. Soc. 113, 113 (1991)

    Article  CAS  Google Scholar 

  37. T. Katsuki, Coord. Chem. Rev. 140, 189 (1995)

    Article  CAS  Google Scholar 

  38. S. Rayati, M. Koliaei, F. Ashouri, S. Mohebbi, A. Wojtczak, A. Kozakiewicz, Appl Cata A: Gen 346, 65 (2008)

    Article  CAS  Google Scholar 

  39. S. Rayati, N. Torabi, A. Ghaemi, S. Mohebbi, A. Wojtczak, Inorg Chem Acta 361, 1239 (2008)

    Article  CAS  Google Scholar 

  40. B. Saito, T. Katsuki, Tetrahedron Lett. 42, 3873 (2001)

    Article  CAS  Google Scholar 

  41. M. Bagherzadeh, L. Tahsini, R. Latifi, Catal. Commun. 9, 1600 (2008)

    Article  CAS  Google Scholar 

  42. R.I. Kureshy, N.H. Khan, S.H.R. Abdi, S.T. Patel, R.V. Jasra, Tetrahedron Asymmetr 12, 433 (2001)

    Article  CAS  Google Scholar 

  43. A. Haimov, R. Neumann, Chem. Commun. 8, 876 (2002)

    Article  Google Scholar 

  44. P. Battioni, J.P. Renaud, J.F. Bartoli, M. Reina-Artiles, M. Fort, D. Mansuy, J. Am. Chem. Soc. 110, 8462 (1988)

    Article  CAS  Google Scholar 

  45. P. O’Brien, D.A. Sweigart, Inorg. Chem. 24, 1405 (1985)

    Article  Google Scholar 

Download references

Acknowledgments

We are thankful for the financial support of Lorestan University of the Islamic Republic of Iran.

Author information

Authors and Affiliations

  1. Department of Chemistry, Lorestan University, Khorramabad, Iran

    Abedien Zabardasti & Sayed Asad Shangaie

Authors
  1. Abedien Zabardasti
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sayed Asad Shangaie
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Abedien Zabardasti.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zabardasti, A., Shangaie, S.A. Synthesis, characterization, spectroscopic and catalytic oxidation studies of Fe(III), Ni(II), Co(III), V(IV) and U(VI) Schiff base complexes with N, O donor ligands derived from 2,3-diaminopyridine. J IRAN CHEM SOC 13, 1875–1886 (2016). https://doi.org/10.1007/s13738-016-0904-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-016-0904-0

Keywords

Search

Navigation