14034-64-1Relevant articles and documents
Nucleophilic Substitution Reaction of Cumyl Arenesulfonates with Anilines
Koh, Han Joong,Lee, Hai Whang,Lee, Ikchoon
, p. 125 - 130 (2007/10/02)
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 ?X > ?'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 nucleophhile concentration is low.