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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 22, Number 3
JKCSEZ 22(3)
June 20, 1978 

 
Title
Nucleophilic Displacement at Sulfur Center (Ⅹ). Solvolysis of Phenylmethanesulfonyl Chloride

황의 친핵성 치환반응 (제10보). 염화페닐메탄술포닐의 가용매분해반응
Author
Ikchoon Lee, Wang Ki Kim

이익춘, 김왕기
Keywords
Abstract
메탄올-물, 에탄올-물, 아세톤-물 및 아세토니트릴-물의 이성분 혼합용매에서 염화페닐메탄술포닐의 가용매분해반응을 속도론적으로 연구하였다. 반응속도는 반양성자용매에서 보다 양성자용매에서 더 빨랐으며, 이온화능력에 대한 반응속도의 감도 즉 Winstein 도시의 m와 전이상태의 용매화수는 양성자용매에서 훨씬 작았다. 이것은 양성자용매의 수소결합용매화에 의한 초기상태의 안정화로서 생각할 수 있다. 반응은 모든 용매계에 있어서 전이상태의 결합형성이 결합파양을 앞지르는 Sn2 메카니즘으로 일어난다 할 수 있다.

The kinetics of phenylmethanesulfonyl chloride in methanol-water, ethanol-water, acetone-water and acetonitrile-water has been investigated. The rate was faster in protic solvents than in aprotic solvents while susceptibility of rate to the ionizing power, i. e., m of the Winstein plot and solvation number of the transition state were much smaller in protic solvents. This was considered in the light of initial state stabilization by hydrogen-bonding solvation of the protic solvents. It was concluded that the reaction proceeds by an SN2 mechanism in which bond-formation precedes bond-breaking at the transition state in all solvent systems.

Page
111 - 116
Full Text
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