Canadian journal of chemistry

Isotope effects in nucleophilic substitution reactions. V. The mechanism of the decomposition of 1-phenylethyldimethylphenylammonium halides in chloroform

HA Joly, KC Westaway

Index: Joly, Helen Alma; Westaway, Kenneth Charles Canadian Journal of Chemistry, 1986 , vol. 64, p. 1206 - 1214

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Citation Number: 5

Abstract

Secondary α and β hydrogen-deuterium kinetic isotope effects have been used together to show that the SN reaction between 1-phenylethyldimethylphenylammonium ion and bromide or iodide ion in chloroform occurs by way of an SN2 mechanism within a triple ion in spite of the fact that it reacts faster than the primary substrate, benzyldimethylphenylammonium bromide. The very loose transition state and steric ...

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