Abstract
Mechanisms of oxidation of stable organic radicals with molecular oxygen are based on a fundamental physical interaction, namely Coulomb interaction. Provided that there is certain structural correspondence between the oxygen molecule and radical center of the substrate, one-electron transfer occurs in the reaction system via the tunneling effect. The electronic structure of unstable triradical generated in the reaction system as a result of one-electron transfer undergoes reorganization into energetically more favorable monoradical structure.
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REFERENCES
Hund, F., Z. Phys., 1927, vol. 40, p. 742. https://doi.org/10.1007/BF01400234
Fowler, R.H. and Nordheim, L., Proc. R. Soc. London, Ser. A, 1928, vol. 119, p. 173. https://doi.org/10.1098/rspa.1928.0091
Fletcher, S.J., Solid State Electrochem., 2010, vol. 14, p. 705. https://doi.org/10.1007/s10008-009-0994-z
Likhtenshtein, G.I., Solar Energy Conversion: Chemical Aspects, Weinheim: Wiley, 2012, p. 1.
Lewis, W.B., Coryell, C.D., and Irvine, J.W., Jr.,J. Chem. Soc., 1949, p. S386. https://doi.org/10.1039/JR949000S386
Randles, J.E.B., Trans. Faraday Soc., 1952, vol. 48, p. 828. https://doi.org/10.1039/TF9524800828
Fletcher, S., Solid State Electrochem., 2007, vol. 11, p. 965. https://doi.org/10.1007/s10008-007-0313-5
Marcus, R.A., J. Electroanal. Chem., 1997, vol. 438, p. 251. https://doi.org/10.1016/S0022-0728(97)00091-0
Zusman, L.D., Chem. Phys., 1980, vol. 49, p. 295. https://doi.org/10.1016/0301-0104(80)85267-0
Bilevich, K.A. and Okhlobystin, O.Yu., Russ. Chem. Rev., 1968, vol. 37, p. 954. https://doi.org/10.1070/RC1968v037n12ABEH001716
Nonhebel, D.C. and Walton, J.C., Free-Radical Chemistry; Structure and Mechanism, Cambridge: Cambridge Univ., 1974.
Ashby, E.C., Acc. Chem. Res., 1988, vol. 21, p. 414. https://doi.org/10.1021/ar00155a005
Pokhodenko, V.D., Ganyuk, L.N., and Brodskii, A.I., Dokl. Akad. Nauk SSSR, 1963, vol. 149, p. 321.
Pokhodenko, V.D., Khizhnyi, V.A., and Bidzilya, V.A., Russ. Chem. Rev., 1968, vol. 37, p. 435. https://doi.org/10.1070/RC1968v037n06ABEH001651
Tanaseichuk, B.S., Pryanichnikova, M.K., and Tikhonova, L.G., Russ. J. Org. Chem., 1999, vol. 35, p. 442.
Tomilin, O.B., Boyarkina, O.V., and Tanaseichuk, B.S., Russ. J. Org. Chem., 2018, vol. 54, p. 719. https://doi.org/10.1134/S1070428018050081
Rozantsev, E.G. and Sholle, V.D., Organicheskaya khimiya svobodnykh radikalov (Organic Chemistry of Free Radicals), Moscow: Khimiya, 1979.
Stephens, P.J., Devlin, F.J., Chablowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, p. 11623. https://doi.org/10.1021/j100096a001
Hehre, W.J., Ditchfield, R., and Pople, J.A., J. Chem. Phys., 1972, vol. 56, p. 2257. https://doi.org/10.1063/1.1677527
Neese, F., Wiley Interdiscip. Rev.: Comput. Mol. Sci., 2012, vol. 2, p. 73. https://doi.org/10.1002/wcms.81
Tanaseichuk, B.S., Tomilin, O.B., Pryanichnikova, M.K., Boyarkina, O.V., and Burtasov, A.A., Russ. J. Org. Chem., 2017, vol. 53, p. 679. https://doi.org/10.1134/S1070428017050062
Tanaseichuk, B.S., Tomilin, O.B., Pryanichnikova, M.K., Tsebulaeva, Y.V., and Boyarkina, O.V., Russ. J. Org. Chem., 2017, vol. 53, p. 764. https://doi.org/10.1134/S1070428017050189
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Tomilin, O.B., Boyarkina, O.V. & Tanaseichuk, B.S. One-Electron Transfer in Reactions of Stable Organic Radicals with Oxygen. Russ J Org Chem 56, 2049–2056 (2020). https://doi.org/10.1134/S1070428020120015
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DOI: https://doi.org/10.1134/S1070428020120015