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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 20, Number 5
JKCSEZ 20(5)
October 20, 1976 

 
Title
Nucleophilic Displacement at Sulfur Center (Ⅷ). Solvolysis of 1-and 2-Naphthalene Sulfonyl Chlorides in Ethanol-Water Mixture

황의 친핵성 치환반응 (제8보). 물-에탄올 혼합용매 속에서 1-및 2-염화나프탈렌 술포닐의 가용매 분해반응
Author
Tae Seop Uhm, Ikchoon Lee, Jae Rok Kim

엄태섭, 이익춘, 김재록
Keywords
Abstract
물-에탄올 혼합용매속에서 1-염화 및 2-염화나프탈렌술포닐의 두 나프틸 화합물의 가용매 분해반응을 전기 전도도법을 사용하여 속도론적으로 연구하였다. 연구결과 2-나프틸 화합물의 반응속도상수가 1-나프틸 화합물의 것보다 컸다. 이것은 MO이론의 예측과는 반대였으며 전이상태에서 1-나프틸 화합물의 peri-hydrogen 효과에 기인된 것으로 설명할 수 있었다. Winstein 그림표의 m값과 Kivinen 그림표의 n값에 의하면 물-에탄올 혼합용매속에서의 두 염화 나프탈렌술포닐의 가용매 분해 치환반응은 Sn2형 반응과정으로 진행된다고 결론지웠다.

Kinetic studies on solvolytic reactions of 1-and 2-naphthalene sulfonyl chlorides in ethanol-water mixtures have been carried out by means of conductometry at several temperatures. The rate constant for 2-naphthyl compound was larger than that for 1-naphthyl compound. This was contrary to the prediction of MO theory and could be rationalized as due to the peri-hydrogen effect in the transition state for 1-naphthyl compound. Based on m values of Winstein plots and n values of Kivinen pacolots it was concluded that the solvolytic displacement of the two naphthalene sulfonyl chlorides in ethanol-water mixtures proceed via SN2 process.

Page
358 - 363
Full Text
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