Current time in Korea 22:41 Jun 13 (Sun) Year 2021 KCS KCS Publications
KCS Publications
My Journal  Log In  Register
HOME > Search > Browsing(BKCS) > Archives

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 

Nucleophilic Substitution Reactions of 1- and 2-Naphtylmethyl Arenesulfonates with Anilines
Hyuck Keun Oh, Se Jeong Song, Chul Ho Shin, Ikchoon Lee
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.
161 - 164
Full Text