KCS Publications

HOME > Search > Browsing(BKCS) > Archives

Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 22, Number 4
BKCSDE 22(4)
April 20, 2001

Title	Nucleophilic Substitution Reactions of Thiophenyl Dimethylacetates and Trimethylacetates with Benzylamines in Acetonitrile
Author	Hyuck Keun Oh, Chi Yeul Park, Jae Myon Lee, Ikchoon Lee
Keywords	Aminolysis, Kinetics and mechanism, Acyl transfer reaction.
Abstract	The kinetics and mechanism of the reactions of thiophenyl dimethylacetates (TDA) and trimethylacetates (TTA) with benzylamines in acetonitrile are studied. The reactions are first order in both the amine and the substrate. Relatively large values of β_X (β_nuc = 1.1-1.5; TDA and 1.1-1.5; TTA) and β_Z (β_lg = -1.8~-2.0; DTA and -1.3~-1.6; TTA) for benzylamines, significantly large k_H/k_D values (=1.2-1.5; DTA and 1.2-1.5; TTA) involving deuterated benzylamines, and large ρ_XZ (=0.82; TDA and 1.05; TTA) values are interpreted to indicate stepwise acyl transfer mechanism, but with the hydrogen bonded four center type transition state for benzylamine. The relatively greater magnitudes of ρ_XZ and the secondary kinetic isotope effects involving deuterated nucleophiles are in line with the proposed mechanism.
Page	383 - 387
Full Text	PDF

How to access to the WOL for The Bulletin of the Korean Chemical Society ?

The Bulletin of the Korean Chemical Society will be co-published with Wiley-VCH from 2015 towards. The online version of the Journal will thus be available on Wiley Online Library, Wiley(-VCH)'s global online platform.

KCS members can get a free online access to the Bulletin of the Korean Chemical Society in WOL.

Free Access to WOL