Abstract
It has been shown, by double zeta quality ab initio MO calculations, that, in the gas phase, a CH bond adjacent to sulphur is more acidic than a CH bond adjacent to oxygen. This trend is in agreement with experimental observations in solution.
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References
Cram, D. J.: Fundamentals of carbanion chemistry. New York: Academic Press 1965
Oae, S., Tagaki, W., Ohno, A.: Tetrahedron 20, 417 (1964)
Coffen, D. L.: Rec. Chem. Progr. 30, 275 (1969); Mitchell, K. A. R.: Chem. Rev. 69, 157 (1969)
Wolfe, S.: Accounts Chem. Res. 5, 102 (1972), and references cited in this article
Tel, L. M., Wolfe, S., Csizmadia, I. G.: J. Chem. Phys. 59, in press (1973)
Wolfe, S., Tel, L. M., Csizmadia, I. G.: Can. J. Chem. 51, 2423 (1973)
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Wolfe, S., Tel, L.M. & Csizmadia, I.G. Gas phase acidities of CH bonds adjacent to oxygen and to sulphur. Theoret. Chim. Acta 31, 355–358 (1973). https://doi.org/10.1007/BF00527562
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DOI: https://doi.org/10.1007/BF00527562