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Статья
2000

Cleavage of Σ-bonds by electroreduction: The EED mechanism


V. V. Yanilkin V. V. Yanilkin , E. A. Berdnikov E. A. Berdnikov , B. I. Buzykin B. I. Buzykin
Российский электрохимический журнал
https://doi.org/10.1007/BF02756896
Abstract / Full Text

The data on the cleavage of Σ-bonds by electroreduction, found in the literature and obtained by the authors, are analyzed. A new EED mechanism is proposed. It is shown, using reactions of reduction of various organic compounds (halogenorganic compounds, ethers, organic phosphates, nitroamines), that this is a rather common reaction path. The EED processes are intermediate between processes EDE and ECE. If the reorganization of reacting species in the first electron transfer is minimal, either E or ECE process is realized; with maximum reorganization, the EDE process; and at intermediate values, the EED process.

Author information
  • Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, ul. Akademika Arbuzova 8, Kazan, 420083, Tatarstan, Russia

    V. V. Yanilkin & B. I. Buzykin

  • Kazan State University, ul. Lenina 18, Kazan, 420008, Tatarstan, Russia

    E. A. Berdnikov

References
  1. Gibson, R.H. and Crosthwaite, J.C.,J. Am. Chem. Soc., 1969, vol. 90, p. 7373.
  2. Supyrev, A.V.,Cand. Sci. (Chem.) Dissertation, Kazan, 1982.
  3. Kargin, Yu.M., Latypova, V.Z., Yakovleva, O.G.,et al., Zh. Obshch. Khim., 1979, vol. 49, p. 2267.
  4. Andrieux, C.P., Blocman, C, Dumas-Bouchiat, J.M., and Saveant, J.-M.,J. Am. Chem. Soc., 1979, vol. 101, p. 3431.
  5. Beland, F.A., Farwell, S.O., and Gallis, P.R.,J. Electroanal. Chem., 1977, vol. 78, p. 145.
  6. Bogoveeva, G.A.,Cand. Sci. (Chem.) Dissertation, Kazan, 1983.
  7. Sease, J.W., Burton, F.G., and Nickol, S.L.,J. Am. Chem. Soc., 1968, vol. 90, p. 2595.
  8. Lawless, J.G., Bartak, D.E., and Hawley, M.D.,J. Am. Chem. Soc., 1969, vol. 91, p. 3431.
  9. Elving, P. and Laone, J.,J. Am. Chem. Soc., 1960, vol. 82, p. 5076.
  10. Gores, G.J., Koeppe, C.E., and Bartak, D.E.,J. Org. Chem., 1979, vol. 44, p. 380.
  11. Galus, Z.,Teoreticzne Podstawy Electroanalizu Chemiczne, Warsaw: Panstw. Wyd. Naukowe, 1971.
  12. Mairanovsky, V.G.,J. Electwanal. Chem., 1981, vol. 125, p. 231.
  13. Mairanovskii, V.G.,Dokl. Akad. Nauk SSSR, 1985, vol. 284, p. 386.
  14. Saveant, J.-M.,J. Am. Chem. Soc., 1987, vol. 109, p. 6788.
  15. Zhuikov, V.V.,Doctoral (Chem.) Dissertation, Kazan, 1996.
  16. Vener, M.V. and Mairanovskii, V.G.,Elektrokhim., 1993, vol. 29, p. 1248.
  17. Andrieux, C.P., Saveant, J.-M., and Su, K.B.,J. Phys. Chem., 1986, vol. 90, p. 3815.
  18. Andrieux, C.P., Merz, A., and Saveant, J.-M.,J. Am. Chem. Soc., 1985, vol. 107, p. 6097.
  19. Occhialini, D., Pederson, S.U., and Lund, H.,Acta Chem. Scand., 1990, vol. 44, p. 715.
  20. Kargin, Yu.M.,Doctoral (Chem.) Dissertation, Kazan, 1971.
  21. Kargin, Yu.M., Kondranina, V.Z., Semakhina, N.I., and Kargina, N.M., Abstracts of Papers,V Vsesoyuz. soveshch. po elektrokhimii (V All-Union Meet. on Electrochem.), Moscow: Proizv.-Izd. Kombinat VINITI, 1974, part 1, p. 193.
  22. Kargin, Yu.M., Latypova, V.Z., and Supyrev, A.V.,Zh. Obshch. Khim., 1984, vol. 52, p. 2623.
  23. Kargin, Yu.M., Kondranina, V.Z., Gafarov, A.N.,et al., Zh. Obshch. Khim., 1997, vol. 47, p. 666.
  24. Garst, J.F., Roberts, R.D., and Pacifi, J.A.,J. Am. Chem. Soc., 1977, vol. 99, p. 3528.
  25. Rusakova, M.S., Tur’yan, Ya.I., and Ustavshchikov, B.F.,Usp. Khim., 1965, vol. 1, p. 854.
  26. Latypova, V.Z., Chichirov, A.A., Zhuikov, V.V.,et al., Zh. Obshch. Khim., 1989, vol. 59, p. 1344.
  27. Zhuikov, V.V., Latypova, V.Z., and Kargin, Yu.M.,Zh. Obshch. Khim., 1990, vol. 60, p. 2759.
  28. Kerr, C.M.L., Webster, K., and Williams, E.,J. Phys. Chem., 1972, vol. 76, p. 2848.
  29. Nekrasov, L.N., Peregudova, S.M., and Yur’eva, L.P., Abstracts of Papers,VII Simpozium “ Dvoinoi sloi i adsorbtsiya na tverdykh elektrodakh ” (VII Symp. on Double Layer and Adsorption at Solid Electrodes), Tartu: Tartu. Gos. Univ., 1985, p. 237.
  30. Rifi, M., inOrganic Electrochemistry: An Introduction and a Guide, Baizer, M.M., Ed., New York: Marcel Dekker, 1973.
  31. Berdnikov, E.A., Fedorov, S.B., and Kargin, Yu.M.,Zh. Obshch. Khim., 1978, vol. 48, p. 875.
  32. Berdnikov, E.A.,Doctoral (Chem.) Dissertation, Kazan: Kazan State Univ., 1989.
  33. Mann, Ch.K. and Barnes, K.K.,Electrochemical Reactions in Nonaqueous Systems, New York: Marcel Dekker, 1970.
  34. Yanilkin, V.V.,Cand. Sci. (Chem.) Dissertation, Kazan: Arbuzov Inst. Org. Phys. Chem., 1979.
  35. Kitagawa, T., Layloff, T., and Adams, R.,Anal. Chem., 1963, vol. 35, p. 1086.
  36. Gores, G.J., Koeppe, CE., and Bartak, D.E.,J. Org. Chem., 1979, vol. 44, p. 380.
  37. Mairanovskii, S.G., Stradins, J.P., and Bezuglyi, V.D.,Polyarografiya v organicheskoi khimii (Polarography in Organic Chemistry), Leningrad: Khimiya, 1975.
  38. Kukharenko, S.V. and Strelets, V.V.,Elektrokhimiya, 1988, vol. 24, p. 1379.
  39. Mishra, S.P. and Symors, M.C.R.,J. Chem. Soc., Perkin Trans. II,1981, p. 185.
  40. Kargin, Yu.M., Kondranina, V.Z., Baitalov, D.A.,et al., Zh. Obshch. Khim., 1977, vol. 47, p. 166.
  41. Medvedev, V.A., Yanilkin, V.V., Babkin, V.A.,et al.,Khim. Drev., 1985, no. 4, p. 82.
  42. Capon, A. and Parsons, R.,J. Electroanal. Chem., 1973, vol. 46, p. 215.
  43. Samuelsson, R. and Sharp, M.,Electrochim. Acta, 1978, vol. 23, p. 315.
  44. Parker, V.D.,Acta Chem. Scand., 1992, vol. 46, p. 307.
  45. Maslak, P. and Narvaez, J.N.,Angew. Chem., 1990, vol. 102, p. 302.
  46. Maslak, P., Kula, J., and Narvaez, J.N.,J. Org. Chem., 1990, vol. 55, p. 2277.
  47. Maslak, P. and Narvaez, J.N.,J. Chem. Soc., Chem. Commun., 1989, p. 138.
  48. Wayner, D.D.M. and Parker, V.D.,Acc. Chem. Res., 1993, vol. 26, p. 287.
  49. Gurvich, L.V., Karachevtsev, G.V., Kondrat’ev, V.N.,et al., Energiya razryva khimicheskikh svyazei: Potentsialy ionizatsii i srodstvo k elektronu (The Cleavage Energy of Chemical Bonds: Ionization Potentials and the Affinity to Electron), Moscow: Nauka, 1974.
  50. Andrieux, C.P., Hapiot, P., and Saveant, J.-M.,J. Phys. Chem., 1988, vol. 92, p. 5987.
  51. Yanilkin, V.V. and Zverev, V.V.,Izv. Akad. Nauk, Ser. Khim., 1999, p. 682.
  52. Mairanovskii, V.G.,Elektrosintez monomerov (Electrosynthesis of Monomers), Moscow: Nauka, 1980, p. 244.
  53. Lund, H., Michel Marie-Andree, and Simonet, J.,Acta Chem. Scand., 1974, vol. 28, p. 900.
  54. Todres, Z.V.,Phosphorus Sulfur Relat. Elem., 1981, vol. 9, p. 353.
  55. Spravochnik po elektrokhimii (A Handbook on Electrochemistry), Sukhotin, A.M., Ed., Leningrad: Khimiya, 1981.
  56. Yanilkin, V.V., Mamedov, V.A., and Berdnikov, E.A., inNovel Trends in Electroorganic Synthesis, Torii, S., Ed., 1998, p. 457.
  57. Kargin, Yu.M., Gritsenko, E.I., Yanilkin, V.V.,et al., Izv. Akad. Nauk SSSR, Ser. Khim., 1992, p. 2023.
  58. Yanilkin, V.V.,Doctoral (Chem.) Dissertation, Kazan: Arbuzov Inst. Org. Phys. Chem., 1998.
  59. Yanilkin, V.V., Maksimyuk, N.I., Gritsenko, E.I., and Kargin, Yu.M.,Izv. Akad. Nauk SSSR, Ser. Khim., 1992, p. 1760.
  60. Wayner, D.D.M., McPhee, D.I., and Griller, D.,J. Am. Chem. Soc., 1988, vol. 110, p. 132.
  61. Budnikov, G.K., Mironova, O.Yu., and Yanilkin, V.V.,Zh. Obshch. Khim., 1992, vol. 62, p. 1099.
  62. Shono, T., Matsumura, Y., Tsubata, K., and Sugiyara, Y.,J. Org. Chem., 1979, vol. 44, p. 4508.
  63. Yanilkin, V.V, Budnikova, Yu.G., Kargin, Yu.M.,et al.,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, p. 1279.
  64. Yanilkin, V.V. and Berdnikov, E.A.,Zh. Obshch. Khim., 1998, vol. 68, p. 32.
  65. Laviron, E. and Fournary, P.,Bull. Soc Chim. Fr., 1966, p. 518.
  66. Laviron, E., Fournary, P., and Greusard, J.,Bull. Soc. Chim. Fr., 1967, p. 1255.