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.
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Literature Cited
T. Bryan (editor), Carcinogenesis: A Comprehensive Survey. Vol. 4, Nitrofurans: Chemistry, Metabolism, Mutagenesis, and Carcinogenesis, Raven Press, New York (1978).
J. E. Biaglow and M. E. Varnes, Free Radicals and Cancer, Marcel Dekker, New York (1982), p. 441.
R. Gavar (Gavars), Ya. P. Stradyn' (Stradins), L. Baumane, and L. Baider, J. Mol. Struct., 102, 183 (1983).
Ya. P. Stadyn' and R. A. Gavar, Advances in the Chemistry of Furan [in Russian], Zinatne, Riga (1978), p. 55.
R. P. Mason and J. L. Holzman, Biochem. Biophys. Rs. Commun., 67, 1267 (1975).
B. Kalynaraman, E. Perez-Reyez, and R. P. Mason, Mol. Pharmacol., 16, 1059 (1979).
W. Kemula and J. Zawadowska, J. Polish Acad. Sci. Bull. Ser. Chem., 23, 275 (1975).
Ya. P. Stradyn' (Stradins), R. A. Gavar (Gavars), and L. Baumane, Electrochim. Acta, 28, 495 (1983).
M. B. Fleisher, R. A. Gavar, A. E. Shvets, and Ya. P.. Stradyn', Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 5, 604 (1977).
V. B. Luzhkov, Zh. Strukt. Khim., 23, 42 (1982).
J. A. Pople and D. L. Beveridge, Approximate MO Theory, McGraw-Hill, New York (1970).
S. H. Glarum and J. H. Marshall, J. Chem. Phys., 41, 2181 (1964).
P. B. Ayscough and F. P. Sargent, J. Chem. Soc., (B), 907 (1966).
D. H. Levy and R. J. Myers, J. Chem. Phys., 42, 3731 (1965).
A. R. Forrester and R. H. Thomson, Nature, 209, 74 (1964).
W. Kemvla and R. Sioda, J. Electroanal. Chem., 6, 183 (1963).
Yu. A. Ustynyuk (editor), Quantum-Chemical Methods for the Calculation of Molecules [in Russian], Khimiya, Msocow (1980), p. 142.
M. Dewar and W. Thier, J. Am. Chem. Soc., 79, 4899 (1977).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1178–1183, September, 1989.
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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
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DOI: https://doi.org/10.1007/BF00487295