Abstract
The kinetics and chlorine isotope effects in the nucleophilic substitution reactions of benzyl and substituted benzyl chlorides with water, cyanide ion, and thiosulfate ion were investigated. For those reactions exhibiting first-order kinetics, the kinetic isotope effect (k35//k37 ) observed was close to 1.0078, while for reactions displaying second-order kinetics the value was 1.0058. Those reactions proceeding by borderline kinetics gave isotope effects intermediate between these two extremes. Detailed analysis of the kinetic and isotope effect data for the reactions with cyanide and thiosulfate ions led to the conclusion that there is a smooth transition in the reaction mechanism from near ideal SN 1 to near ideal SN 2 as the electrondonating power of the substituent decreases. It appeared that the magnitude of the chlorine isotope effect may be used to differentiate between SN 1 and SN 2 reactions.
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