|
KMID : 1059519850290020088
|
|
Journal of the Korean Chemical Society
1985 Volume.29 No. 2 p.88 ~ p.97
|
|
|
Kinetic Study on Nucleophilic Substitution of 1-Anthracenesulfonyl Chloride with Anilines
|
|
Kim Hyong-Tae
Yoh Soo-Dong
|
|
|
Abstract
|
|
|
|
1-Anthracenesulfonyl chloride used as a substrate has been prepared from anthra-quinone, and its melting point (124℃) was confirmed to be considerably different from the literature value (90℃). Rates of nucleophilic substitution reactions of this substrate with some p-substituted anilines in dry acetone were determined by electroconductometric method, and their mechanism has been discussed. As a result, it has been found that these reactions proceed in parallel catalyzed by anilines together with noncatalyzed process, and that their catalytic activities are electrophilic. Judging from Brφnsted β (0.77), Hammett ρ(-3.2), and activation parameters which were determined from the temperature dependence of noncatalyzed second order rate constants, it appears most appropriate that their mechanism should be discussed in terms of an associative SN2 involving sulfonylammonium intermediate.
|
|
|
KEYWORD
|
|
|
|
|
|
FullTexts / Linksout information
|
|
|
|
|
|
Listed journal information
|
|
|