Skip to main content
Log in

New sulfanyl- and selanyl-substituted Schiff bases derived from 2-chalcogenoalkylamines and aromatic aldehydes. Synthesis and complex formation reactions

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A number of β-phenyl(or benzyl)selanyl- and β-phenylsulfanyl-substituted imines possessing an additional donor nitrogen, oxygen, or sulfur atom were synthesized by reaction of 2-phenylsulfanylethanamine, 2-phenylsulfanylcyclohexanamine, 2-phenylselanylcyclohexanamine, and 2-benzylselanylaniline with salicylaldehyde, 2-pyridinecarbaldehyde, or 2-tert-butylsulfanylbenzaldehyde. The resulting Schiff bases were tested as ligands in the complex formation with nickel(II) and copper(II), and mononuclear (L-H)MCl or LMCl2 coordination compounds were isolated (L = sulfur- or selenium-containing imine). The redox properties of the selenium-containing ligands and complexes were studied by cyclic voltammetry. The complexes were found to undergo reduction of the metal ion in two one-electron steps. The reduction is reversible for copper complexes and irreversible for nickel complexes.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Jørgensen, A.K., Chem. Rev., 1989, vol. 89, no. 3, p. 431.

    Article  Google Scholar 

  2. Pospisil, P.J., Carsten, D.H., and Jacobsen, E.N., Chem. Eur. J., 1996, vol. 2, no. 8, p. 974.

    Article  CAS  Google Scholar 

  3. Bryliakov, K.P. and Talsi, E.P., Inorg. Chem., 2003, vol. 42, no. 22, p. 7258.

    Article  CAS  Google Scholar 

  4. Doyle, M.P., Chem. Rev., 1986, vol. 86, no. 5, p. 919.

    Article  CAS  Google Scholar 

  5. Evans, D.A., Faul, M.M., and Bilodeau, M.T., J. Am. Chem. Soc., 1994, vol. 116, no. 7, p. 2742.

    Article  CAS  Google Scholar 

  6. Evans, D.A., Faul, M.M., and Bilodeau, M.T., J. Org. Chem., 1991, vol. 56, no. 24, p. 6744.

    Article  CAS  Google Scholar 

  7. Fukuda, T. and Katsuki, T., Tetrahedron Lett., 1997, vol. 38, no. 19, p. 3435.

    Article  CAS  Google Scholar 

  8. Schaus, S.E., Brenalt, J., and Jacobsen, E.N., J. Org. Chem., 1998, vol. 63, no. 2, p. 403.

    Article  CAS  Google Scholar 

  9. Kaufman, M.D., Grieco, P.A., and Bougie, D.W., J. Am. Chem. Soc., 1993, vol. 115, no. 24, p. 11 648.

    Article  CAS  Google Scholar 

  10. Larrow, J.F. and Jacobsen, E.N., J. Am. Chem. Soc., 1994, vol. 116, no. 26, p. 12 129.

    Article  CAS  Google Scholar 

  11. Jacobsen, E.N., Kakiuchi, F., Konsler, R.G., Larrow, J.F., and Tokunaga, M., Tetrahedron Lett., 1997, vol. 38, no. 5, p. 773.

    Article  CAS  Google Scholar 

  12. Tokunaga, M., Larrow, J.F., Kakiuchi, F., and Jacobsen, E.N., Science, 1997, vol. 277, no. 8, p. 936.

    Article  CAS  Google Scholar 

  13. Leighton, J.L. and Jacobsen, E.N., J. Org. Chem., 1996, vol. 61, no. 1, p. 389.

    Article  CAS  Google Scholar 

  14. Martinez, L.E., Leighton, J.L., Carsten, D.H., and Jacobsen, E.N., J. Am. Chem. Soc., 1995, vol. 117, no. 21, p. 5897.

    Article  CAS  Google Scholar 

  15. Paddock, R.L. and Nguyen, S.B.T., J. Am. Chem. Soc., 2001, vol. 123, no. 46, p. 11 498.

    Article  CAS  Google Scholar 

  16. Darensbourg, D.J. and Holtcamp, M.W., Coord. Chem. Rev., 1996, vol. 153, p. 155.

    Article  CAS  Google Scholar 

  17. Butin, K.P., Moiseeva, A.A., Beloglazkina, E.K., Chudinov, Yu.B., Chizhevskii, A.A., Mironov, A.V., Tarasevich, B.N., Lalov, A.V., and Zyk, N.V., Izv. Akad. Nauk, Ser. Khim., 2005, no. 1, p. 169.

    Google Scholar 

  18. Dewar, M.J.S., Healy, E.F., and Stewart, J.J.P., J. Comput. Chem., 1984, vol. 5, no. 4, p. 358.

    Article  CAS  Google Scholar 

  19. Chernysheva, A.N., Antipin, R.L., Borisenko, A.A., Beloglazkina, E.K., and Zyk, N.V., Izv. Akad. Nauk, Ser. Khim., 2011, no. 1, p. 189.

    Google Scholar 

  20. Amosova, S.V., Makhaeva, N.A., Martynov, A.V., Potapov, V.A., Steele, B.R., and Kostas, I.D., Synthesis, 2005, no. 10, p. 1641.

    Google Scholar 

  21. Carlans, M.W., Robyn, L.M., and Schiesser, C.H., Org. Biomol. Chem., 2004, vol. 2, no. 18, p. 2612.

    Article  Google Scholar 

  22. Meth-Cohn, O. and Tarnowski, B., Synthesis, 1978, no. 1, p. 56.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. K. Beloglazkina.

Additional information

Original Russian Text © A.N. Chernysheva, E.K. Beloglazkina, R.L. Antipin, A.A. Moiseeva, N.V. Zyk, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 2, pp. 257–264.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chernysheva, A.N., Beloglazkina, E.K., Antipin, R.L. et al. New sulfanyl- and selanyl-substituted Schiff bases derived from 2-chalcogenoalkylamines and aromatic aldehydes. Synthesis and complex formation reactions. Russ J Gen Chem 83, 311–318 (2013). https://doi.org/10.1134/S1070363213020138

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363213020138

Keywords

Navigation