Correlation of isotope effects in substitution reactions with nucleophilicities. Secondary α-deuterium isotope effect in the iodide-131 exchange of methyl-d₃ iodide

Abstract

The secondary α-deuterium isotope effect in iodide-131 exchange of methyl-d 3 iodide is k H /k D = 1.05 ± 0.01 in methanol and 1.10 ± 0.04 in water at 20°. A correlation of secondary α-deuterium and 13 C effects, in bimolecular nucleophilic substitution reactions, with the difference of E values between nucleophile and leaving group is presented.

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