Kinetic Isotope Effects in the Nucleophilic Substitution Reactions of Benzyl- and 1- phenylethyl 뻖enzenesulfonates with Deuterated Aniline Nucleophiles

초록

Primary and secondary a-deuterium kinetic isotopo effects are determined with deuterated aniline nucleophiles in the nucleophilic substitution reactions of benzyl benzensulfonates and 1-phenylethyl benzenesulfonates in acetonitrile 30.0℃ The kH/kD values support our previous conclusions regarding the transition state structures proposed for the two reactions based on the cross-interaction constants ρij; the former is a typical Sn2 reaction whereas in the latter the four-center transition state may be involved.