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One-Electron Transfer in Reactions of Stable Organic Radicals with Oxygen

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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

  1. Hund, F., Z. Phys., 1927, vol. 40, p. 742. https://doi.org/10.1007/BF01400234

    Article  CAS  Google Scholar 

  2. 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

    Article  CAS  Google Scholar 

  3. Fletcher, S.J., Solid State Electrochem., 2010, vol. 14, p. 705. https://doi.org/10.1007/s10008-009-0994-z

    Article  CAS  Google Scholar 

  4. Likhtenshtein, G.I., Solar Energy Conversion: Chemical Aspects, Weinheim: Wiley, 2012, p. 1.

  5. Lewis, W.B., Coryell, C.D., and Irvine, J.W., Jr.,J. Chem. Soc., 1949, p. S386. https://doi.org/10.1039/JR949000S386

  6. Randles, J.E.B., Trans. Faraday Soc., 1952, vol. 48, p. 828. https://doi.org/10.1039/TF9524800828

    Article  CAS  Google Scholar 

  7. Fletcher, S., Solid State Electrochem., 2007, vol. 11, p. 965. https://doi.org/10.1007/s10008-007-0313-5

    Article  CAS  Google Scholar 

  8. Marcus, R.A., J. Electroanal. Chem., 1997, vol. 438, p. 251. https://doi.org/10.1016/S0022-0728(97)00091-0

    Article  CAS  Google Scholar 

  9. Zusman, L.D., Chem. Phys., 1980, vol. 49, p. 295. https://doi.org/10.1016/0301-0104(80)85267-0

    Article  CAS  Google Scholar 

  10. Bilevich, K.A. and Okhlobystin, O.Yu., Russ. Chem. Rev., 1968, vol. 37, p. 954. https://doi.org/10.1070/RC1968v037n12ABEH001716

    Article  Google Scholar 

  11. Nonhebel, D.C. and Walton, J.C., Free-Radical Chemistry; Structure and Mechanism, Cambridge: Cambridge Univ., 1974.

  12. Ashby, E.C., Acc. Chem. Res., 1988, vol. 21, p. 414. https://doi.org/10.1021/ar00155a005

    Article  CAS  Google Scholar 

  13. Pokhodenko, V.D., Ganyuk, L.N., and Brodskii, A.I., Dokl. Akad. Nauk SSSR, 1963, vol. 149, p. 321.

    CAS  Google Scholar 

  14. Pokhodenko, V.D., Khizhnyi, V.A., and Bidzilya, V.A., Russ. Chem. Rev., 1968, vol. 37, p. 435. https://doi.org/10.1070/RC1968v037n06ABEH001651

    Article  Google Scholar 

  15. Tanaseichuk, B.S., Pryanichnikova, M.K., and Tikhonova, L.G., Russ. J. Org. Chem., 1999, vol. 35, p. 442.

    CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. Rozantsev, E.G. and Sholle, V.D., Organicheskaya khimiya svobodnykh radikalov (Organic Chemistry of Free Radicals), Moscow: Khimiya, 1979.

  18. 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

    Article  CAS  Google Scholar 

  19. Hehre, W.J., Ditchfield, R., and Pople, J.A., J. Chem. Phys., 1972, vol. 56, p. 2257. https://doi.org/10.1063/1.1677527

    Article  CAS  Google Scholar 

  20. Neese, F., Wiley Interdiscip. Rev.: Comput. Mol. Sci., 2012, vol. 2, p. 73. https://doi.org/10.1002/wcms.81

    Article  CAS  Google Scholar 

  21. 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

    Article  CAS  Google Scholar 

  22. 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

    Article  CAS  Google Scholar 

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Correspondence to O. B. Tomilin.

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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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