Skip to main content
Log in

Detection of nitrosofuran anion radicals in the electrochemical reduction of 5-nitrofuran. EPR investigations and quantum-chemical calculations

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Previously unknown radicals that are associated with the 5-N-furylhydroxylamine-5-nitrosofuran redox system were detected by EPR spectroscopy in the electrochemical reduction of 5-nitrofuran. The electron structures of the free-radical products of the reduction of 5-nitrofuran were calculated by the INDO method. On the basis of the hyperfine structures (hfs) of the EPR spectra and the results of quantum-chemical calculations it was concluded that 5-nitrosofuran anion radicals and the nitrosofuran dimer were recorded.

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

Literature Cited

  1. T. Bryan (editor), Carcinogenesis: A Comprehensive Survey. Vol. 4, Nitrofurans: Chemistry, Metabolism, Mutagenesis, and Carcinogenesis, Raven Press, New York (1978).

    Google Scholar 

  2. J. E. Biaglow and M. E. Varnes, Free Radicals and Cancer, Marcel Dekker, New York (1982), p. 441.

    Google Scholar 

  3. R. Gavar (Gavars), Ya. P. Stradyn' (Stradins), L. Baumane, and L. Baider, J. Mol. Struct., 102, 183 (1983).

    Google Scholar 

  4. Ya. P. Stadyn' and R. A. Gavar, Advances in the Chemistry of Furan [in Russian], Zinatne, Riga (1978), p. 55.

    Google Scholar 

  5. R. P. Mason and J. L. Holzman, Biochem. Biophys. Rs. Commun., 67, 1267 (1975).

    Google Scholar 

  6. B. Kalynaraman, E. Perez-Reyez, and R. P. Mason, Mol. Pharmacol., 16, 1059 (1979).

    Google Scholar 

  7. W. Kemula and J. Zawadowska, J. Polish Acad. Sci. Bull. Ser. Chem., 23, 275 (1975).

    Google Scholar 

  8. Ya. P. Stradyn' (Stradins), R. A. Gavar (Gavars), and L. Baumane, Electrochim. Acta, 28, 495 (1983).

    Google Scholar 

  9. M. B. Fleisher, R. A. Gavar, A. E. Shvets, and Ya. P.. Stradyn', Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 5, 604 (1977).

    Google Scholar 

  10. V. B. Luzhkov, Zh. Strukt. Khim., 23, 42 (1982).

    Google Scholar 

  11. J. A. Pople and D. L. Beveridge, Approximate MO Theory, McGraw-Hill, New York (1970).

    Google Scholar 

  12. S. H. Glarum and J. H. Marshall, J. Chem. Phys., 41, 2181 (1964).

    Google Scholar 

  13. P. B. Ayscough and F. P. Sargent, J. Chem. Soc., (B), 907 (1966).

  14. D. H. Levy and R. J. Myers, J. Chem. Phys., 42, 3731 (1965).

    Google Scholar 

  15. A. R. Forrester and R. H. Thomson, Nature, 209, 74 (1964).

    Google Scholar 

  16. W. Kemvla and R. Sioda, J. Electroanal. Chem., 6, 183 (1963).

    Google Scholar 

  17. Yu. A. Ustynyuk (editor), Quantum-Chemical Methods for the Calculation of Molecules [in Russian], Khimiya, Msocow (1980), p. 142.

    Google Scholar 

  18. M. Dewar and W. Thier, J. Am. Chem. Soc., 79, 4899 (1977).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1178–1183, September, 1989.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Isichenko, T.S., Baider, L.M. & Luzhkov, V.B. Detection of nitrosofuran anion radicals in the electrochemical reduction of 5-nitrofuran. EPR investigations and quantum-chemical calculations. Chem Heterocycl Compd 25, 983–988 (1989). https://doi.org/10.1007/BF00487295

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00487295

Keywords

Navigation