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References
Recent studies include: Bell, R. P.: The proton in chemistry. 2nd Ed. New York: Cornell University Press 1973
Caldin, E. F., Gold, V., (eds.): Proton transfer reactions. London: Chapman and Hall 1975
Proton transfer: Faraday Symposium of the Chemical Society, No. 10 (1975)
A highly relevant discussion of gas-phase H atom transfer isotope effects is Johnston, H. S.: Gas phase reaction rate theory. Chap. 13. New York: Ronald Press 1966
Biegeleisen, J.: J. Chem. Phys. 17, 675 (1949)
Theoretical evidence for linearity of H atom transfer transition states, Ref. 2), Chap. 10. The evidence for linearity of proton transfer transition states is based upon analogy to the inverting SN2 reactions on carbon, the linearity of HF −2 etc., as well as electrostatic and orbital considerations
Lewis, E. S., Symons, M. C. R.: Quart. Revs. 12, 230 (1958); Hawthorne, M. F., Lewis, E. S.: J. Am. Chem. Soc. 80, 4296 (1958); Olah, G. A., Halpern, Y., Shen, J., Mo, Y. K.; J. Am. Chem. Soc. 93, 1251 (1971)
Lewis, E. S., Kozuka, S., among others: J. Am. Chem. Soc. 95, 282 (1973)
Lewis, E. S., Shen, C. C.: J. Am. Chem. Soc. 99, 3055 (1977)
Westheimer, F. H.: Chem. Rev. 61, 265 (1961)
Bell, R. P.: The proton in chemistry. 2nd edit. New York: Cornell University Press 1973, p. 267 ff.
Willi, A. V.: Helv. Chim. Acta 34, 1220 (1971)
Lewis, E. S., Chap. 4 in: Isotopes in hydrogen transfer processes. Vol. 2 of: Isotopes in organic chemistry, Buncel, E., Lee, C. C., (eds.). Amsterdam: Elsevier 1976
Lewis, E. S.: Chap. 10 in Ref. 1b)
More O'Ferrall, R. A.: p. 238, Ref. 1b)
We ignore the case that v ‡1 H>v HX; it seems unrealistic
An example in which a k H/kD of 10 is divided about equally between the tunnel correction and the semiclassical isotope effect for a hydride transfer is given in: Lewis, E. S., Robinson, J. K.: J. Am. Chem. Soc. 90, 4337 (1968)
Marcus, R. A.: J. Chem. Phys. 24, 966 (1956)
Kreevoy, M. M., Oh, S.: J. Am. Chem. Soc. 95, 4805 (1973)
Marcus, R. A.: J. Phys. Chem. 72, 891 (1968); Marcus, R. A., Chapt. 1 in: Technique of chemistry. Vol. VI. Investigations of rates and mechanisms of reactions. Lewis, E. S. (ed.). New York: Wiley-Interscience 1974
Ref. 2) Chap. 10
Lewis, E. S., More O'Ferrall, R. A., Shen, C. C.: in preparation; Chu, C. C.: Ph. D. Thesis, Rice University, 1976; Lewis, E. S., More O'Ferrall, R. A.: paper presented at A.C.S. SW Regional Meeting, El Paso, 1973
This relation between variable isotope effects with a maximum and plausibly non-linear free energy relation was qualitatively noted in connection with proton transfers: Lewis, E. S., Funderburk, L. H.: J. Am. Chem. Soc. 89, 2322 (1967). Marcus18) correctly points out that the reference to diffusion control is irrelevant
Swain, C. G., Stivers, E. C., Renwer, J. F., Schaad, L. J.: J. Am. Chem. Soc. 80, 5885 (1955)
Lewis, E. S., Robinson, J. K.: J. Am. Chem. Soc. 90, 4337 (1968); Jones, J. R.: Trans. Faraday Soc. 65, 2138 (1969)
Pryor, W. A., Kneipp, K. G.: J. Am. Chem. Soc. 93, 5584 (1971)
Lewis, E. S., Ogino, K.: J. Am. Chem. Soc. 98, 2260 (1976)
Glaspie, P. S.: Ph. D. Thesis, Rice University, 1974
Wieland, H.: Ber. 42, 3020 (1909); Pinck, L. A.: J. Am. Chem. Soc. 55, 1711 (1933)
Lewis, E. S., Butler, M. M.: Chem. Comm. 1971, 941
Russell, G. A., in: Free radicals. Kochi, J. K. (ed.). New York: Wiley-Interscience 1973, p. 312
Carlsson, D. J., Howard, J. A., Ingold, K. U.: J. Am. Chem. Soc. 88, 4725 (1966)
Kerr, J. A., in: Free radicals. Vol. I. Kochi, J. K. (ed.). New York: Wiley-Interscience 1973, p. 15
Quoted by Simonyi, M., Tüdos, F.: Adv. Phys. Org. Chem. 9, 127 (1970)
Kozuka, S., Lewis, E. S.: J. Am. Chem. Soc. 98, 2254 (1976)
Lewis, E. S., Nieh, E. C.: J. Am. Chem. Soc. 98, 2268 (1976)
Added in proof: Values of S-H bond energies have recently been revised upward by more than 5 Kcal/mole. If all else is unchanged, the estimate of the trityl-H bond energy should be correspondingly increased
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Lewis, E.S. (1978). Isotope effects in hydrogen atom transfer reactions. In: Organic Compunds. Topics in Current Chemistry, vol 74. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0050145
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DOI: https://doi.org/10.1007/BFb0050145
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