Abstract
The dependence of the degree of charge transfer in substituted alkanes on the relative positions and electron-donor (or acceptor) properties of the groups eliminated in β-elimination reactions has been studied. Rules obtained from the generalized principle of maximum overlap have been used for the analysis of the relations between the coefficients in front of the basis functions in the expansions of the MOs. It has been established that trans elimination is observed in the case of substituents with pronounced electron-acceptor and electron-donor properties. In heterogeneous-catalytic reactions the nature of the active sites on the surface of the catalyst strongly influences the electron-donor (or acceptor) properties of the groups being eliminated. The catalytic dehydrochlorination of 1,1,2-trichloroethane has been considered as an example.
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Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vol. 22, No. 2, pp. 168–174, March–April, 1986.
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Shatkovskaya, D.B., Gineitite, V.L. & Bolotin, A.B. Application of the generalized principle of maximum overlap to the study of the stereochemistry of β-elimination reactions. Theor Exp Chem 22, 157–162 (1986). https://doi.org/10.1007/BF00519186
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DOI: https://doi.org/10.1007/BF00519186