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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 18, Number 2
BKCSDE 18(2)
February 20, 1997 

 
Title
Nucleophilic Substitution Reactions of 1- and 2-Naphtylmethyl Arenesulfonates with Anilines
Author
Hyuck Keun Oh, Se Jeong Song, Chul Ho Shin, Ikchoon Lee
Keywords
Abstract
Kinetic studies are carried out on the reactions of 1- and 2-naphthylmethyl arenesulfonates with anilines in acetonitrile at 25.0 ℃. The rates are faster for the 2-naphthylmethyl series than for the corresponding 1-naphthylmethyl series suggesting that there is a greater stabilization of positive charge development in the TS at the arylmethyl reaction center carbon for the former. The sign and magnitude of ρxz (=-0.12) are similar to those of the benzylic series. Thus, benzyl, 1- and 2-naphthylmethyl derivatives belong to a class of compounds which react with aniline nucleophiles through a relatively loose SN2 TS. Kinetic secondary deuterium isotope effects indicated that a stronger nucleophile and nucleofuge lead to a later TS as the definition of ρxz requires.
Page
161 - 164
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