Single Electron Transfer in Aliphatic Nucleophilic Substitution

  • Henning Lund
Part of the NATO ASI Series book series (NSSA, volume 197)


Since the classical studies by Ingold in the nineteen thirties the mechanism of the aliphatic nucleophilic substitution reaction has been described as a polar two-electron mechanism in which the nucleophile transfers two electrons to the new bond which is established to the electrophilic center. Depending on the reaction order the abbreviations SN1 and SN2 were used for first-order and second-order reactions, respectively.


Alkyl Halide Dynamic Nuclear Polarization Benzyl Chloride Reorganization Energy Single Electron Transfer 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1a.
    N. Kornblum, R.E. Michel, and R.C. Kerber, J. Am. Chem. Soc. 88: 5660, 5662 (1966).CrossRefGoogle Scholar
  2. b.
    N. Kornblum, Angellw. Chem. 87: 797 (1975).CrossRefGoogle Scholar
  3. c.
    G.A. Russell and W.C. Danen, J. Am. Chem. Soc. 88: 5663 (1966).CrossRefGoogle Scholar
  4. 2.
    G.A. Russell, M. Jawdosiuk, and M. Makosza, J. Am. Chem. Soc. 101: 2355 (1979).CrossRefGoogle Scholar
  5. 3a.
    G.A. Russell and G.W. Holland, J. Am. Chem. Soc. 91: 3967 (1969).CrossRefGoogle Scholar
  6. b.
    H.R. Ward, R.G. Lawler, and R.A. Cooper, J. Am. Chem. Soc. 91: 746 (1969).CrossRefGoogle Scholar
  7. c.
    A.R. Lepley and R.L. Landau, J. Am. Chem. Soc. 91: 748 (1969).CrossRefGoogle Scholar
  8. 4.
    S. Bank and D.A. Noyd, J. Am. Chem. Soc. 95: 8203 (1973).CrossRefGoogle Scholar
  9. 9a.
    J.F. Garst, Acc. Chem. Res. 4:400 (1971) and references therein.CrossRefGoogle Scholar
  10. b.
    S. Bank and D.A. Juckett, J. Am. Chem. Soc. 89: 7742 (1976).CrossRefGoogle Scholar
  11. 6a.
    H. Lund, M.A. Michel, and J. Simonet, Acta Chem. Scand. B28: 900 (1974).CrossRefGoogle Scholar
  12. b.
    J. Simonet, M.A. Michel, and H. Lund, Acta Chem. Scand. B29: 489 (1975).CrossRefGoogle Scholar
  13. c.
    H. Lund and J. Simonet, J. Electroanal. Chem. 65: 205 (1975).CrossRefGoogle Scholar
  14. d.
    H. Lund, J. Mol. Cat. 38: 203 (1986).CrossRefGoogle Scholar
  15. 7.
    H. Lund and L.H. Kristensen, Acta Chem. Scand. B33: 495 (1979).CrossRefGoogle Scholar
  16. 8.
    L. Eberson, Acta Chem. Scand. B38: 439 (1984).CrossRefGoogle Scholar
  17. 9a.
    T. Lund and H. Lund, Acta Chem. Scand. B40: 470 (1986);CrossRefGoogle Scholar
  18. T. Lund and H. Lund, Acta Chem. Scand. B41: 93 (1987);CrossRefGoogle Scholar
  19. T. Lund and H. Lund, Acta Chem. Scand. B42: 269 (1988).CrossRefGoogle Scholar
  20. b.
    K. Daasbjerg, T. Lund, and H. Lund, Tetrahedron Lett. 30: 493 (1989).CrossRefGoogle Scholar
  21. c.
    R. Fuhlendorff, D. Occhialini, S.U. Pedersen, and H. Lund, Acta Chem. Scand. B43 (1989), 803.CrossRefGoogle Scholar
  22. d.
    T. Lund, S.U. Pedersen, H. Lund, K.M. Cheung, and J.H.P. Utley, Acta Chem. Scand. B41: 285 (1987).CrossRefGoogle Scholar
  23. 10a.
    A. Pross and S.S. Shaik, Acc. Chem. Res. 16: 363 (1983).CrossRefGoogle Scholar
  24. b.
    A. Pross, Acc. Chem. Res. 18: 212 (1985).CrossRefGoogle Scholar
  25. 11a.
    J.F. Bunnett, Acc. Chem. Res. 11: 413 (1978).CrossRefGoogle Scholar
  26. b.
    J.-M. Savéant, Acc. Chem. Res. 13: 323 (1980).CrossRefGoogle Scholar
  27. 12.
    L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer Verlag, Berlin, Heidelberg (1987)CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Henning Lund
    • 1
  1. 1.Department of Organic ChemistryUniversity of ÅrhusÅrhus CDenmark

Personalised recommendations