Steric Versus Electronic Components of Secondary Deuterium Isotope Effects Depend on the Size of Electrophilic Probes

  • Alexandru T. Balaban


Isotope effects have become important for elucidating reaction mechanisms, for increasing the biological half-life of drugs, for studying metabolic pathways, etc. Several books 1 and reviews 2 have been devoted to isotope effects.


Isotope Effect Electronic Component Methyl Iodide Nitrogen Heteroatom Nuclear Magnetic Resonance Shift 
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  1. 1.
    L. Melander, “Isotope Effects on Reaction Rates”, The Ronald Press Co., New York, 1960Google Scholar
  2. C. J. Collins and N. S. Bowman (eds.) “Isotope Effects in Chemical Reactions”, Van Nostrand - Reinhold, New York, 1970Google Scholar
  3. A. F. Thomas, “Deuterium Labeling in Organic Chemistry”, Appleton-Century-Crofts, New York, 1971, p. 401.Google Scholar
  4. 2.
    C. J. Collins, Adv. Phys. Org. Chem. 2: 63 (1964)Google Scholar
  5. E. R. Thornton, Ann. Rev. Phys. Chem. 17: 349 (1968)CrossRefGoogle Scholar
  6. E. A. Halevi, Progr. Phys. Org. Chem. 1: 150 (1963)Google Scholar
  7. 3.
    L. S. Bartell, K. Kuchitsu and R. J. de Neui, J. Chem. Phys . 35: 1211 (1961)CrossRefGoogle Scholar
  8. L. S. Bartell, E. A. Roth, C. D. Hollowell, K. Kuchitsu and J. E. Young, Ibid. 42: 2693 (1965)Google Scholar
  9. L. S. Bartell, J. Am. Chem. Soc . 83: 3567 (1971)Google Scholar
  10. K. Clausius and K. Weigand, Z. physik. Chem. B 46: 1 (1940)Google Scholar
  11. P. J. Mitchell and L. Phillips, Chem. Commun . 90: 8 (1975).Google Scholar
  12. 4.
    E. A. Halevi, N. Nussim and A. Ron, J. Chem, Soc . 8: 66 (1963)Google Scholar
  13. B. D. Batts and E. Spinner, Ibid. 7: 89 (1968).Google Scholar
  14. 5.
    A. T. Balaban, J. Labelled Comp. Radiopharm . 18: 1621 (1981).CrossRefGoogle Scholar
  15. 6.
    A. Gero and J. J. Markham, J. Org. Chem. 16: 1735 (1951)Google Scholar
  16. M. Tamres, S. Searles, E. M. Leighly and L. W. Mohrman, J. Am. Chem. Soc . 76: 3983 (1954).CrossRefGoogle Scholar
  17. 7.
    A. T. Balaban, I. I. Stânoiu and E. Gârd, Rev. Roumaine Chim. 22: 1191 (1977).Google Scholar
  18. 8.
    H. C. Brown, J. Chem. Soc . 12: 48 (1956)Google Scholar
  19. L. W. Deady and J. Zoltewicz, J. Org. Chem . 37: 603 (1972)CrossRefGoogle Scholar
  20. J. A. Zoltewicz and L. W. Deady, Adv. Heterocyclic Chem. 22: 71, 85 (1978)Google Scholar
  21. G. W. Duff in, ibid. 3: 1 (1964).Google Scholar
  22. 9.
    A. T. Balaban, A. Bota, D. C. Oniciu, G. Klatte, C. Roussel and J. Metzger, J. Chem. Res . 8: 44 (1981)Google Scholar
  23. 10.
    H. C. Brown and G. J. Mc Donald, J. Am. Chem. Soc . 88: 2514 (1966).Google Scholar
  24. 11.
    C. C. Hinckley, W. A. Boyd, G. V. Smith and F. Behbahany, in “Nuclear Magnetic Resonance Shift Reagents”, R. E. Sievers, ed., Academic Press, New York, 1973, p. 1;CrossRefGoogle Scholar
  25. G. V. Smith, W. A. Boyd and C. C. Hinckley, J. Am. Chem. Soc . 93: 6319 (1971).Google Scholar
  26. 12.
    A. T. Balaban and M. D. Gheorghiu, unpublished data.Google Scholar
  27. 13.
    A. T. Balaban, I. I. Stânoiu and F. Chiraleu, Chem. Commun . 984 (1976).Google Scholar
  28. A. T. Balaban, I. I. Stânoiu and F. Chiraleu, Rev. Roumaine Chim. 23: 187 (1978).Google Scholar

Copyright information

© Springer Science+Business Media New York 1985

Authors and Affiliations

  • Alexandru T. Balaban
    • 1
  1. 1.Organic Chemistry DepartmentPolytechnic InstituteBucharest 16Roumania

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