Carbon-13 kinetic isotope effects. V. Substituent effects on k12/k13 for alcoholysis of 1-phenyl-1-bromoethane

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Abstract
As a test of our earlier interpretations of the 13C kinetic isotope effects found for alcoholysis of 1-phenyl-1-bromoethane, we have examined the effect of the p-methyl and p-bromo substituents on the 13C fractionations in ethanol and methanol. Isotopic fractionation at the α-carbon is found to be substituent dependent, and the observed trend is consistent with the proposal that stabilization of the cationic center by the phenyl ring is a major factor governing the isotope effect in these systems. The first example of an inverse primary kinetic isotope effect for carbon (k12/k13 < 1) is described.

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