Abstract
The nucleophilic substitution reaction of cumyl arenesulfonate with aniline has been investigated. The reaction in acetonitrile proceeds by the SN2 mechanism with probable frontside nucleophilic attack. The large magnitude of ρxz(=–0.75) obtained results in an observable sign reversal of ρz at x= 0.83, with a negative ρz value for σx > x. This rather unusual phenomenon can be rationalized by a strong interaction between the nucleophile and leaving group due to their close proximity in the transition state, which in turn is a result of the frontside nucleophilic attack. The reactions in methanol indicate that the SN1 channel competes with the SN2 pathway and ion-pair return is observed when the aniline nucleophile concentration is low.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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