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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 11, Number 5
BKCSDE 11(5)
May 20, 1990 

Kinetic Isotope Effects in the Nucleophilic Substitution Reactions of Benzyl- and 1-Phenylethyl -benzenesulfonates with Deuterated Aniline Nucleophiles
Ikchoon Lee*, Han Joong Koh, Bon-Su Lee, Hai Whang Lee, Jae Ho Choi
Primary and secondary α-deuterium kinetic isotope effects are determined with deuterated aniline nucleophiles in the nucleophilic substitution reactions of benzyl benzenesulfonates and 1-phenylethyl benzenesulfonates in acetonitrile at 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.
435 - 438
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