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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 20, Number 1
JKCSEZ 20(1)
February 20, 1976 

 
Title
Nucleophilic Displacement at Sulfur Center (Ⅶ). Conformation and Ethanolysis of Benzenesulfenyl Chloride

유기 황화합물의 친핵성 치환반응 (제7보). 염화벤젠술페닐의 형태와 가에탄올 분해
Author
Ikchoon Lee, Jae Eui Yie, Dae Hyung Chung

이익춘, 이재의, 정대형
Keywords
Abstract
염화벤젠술페닐의 바람직한 형태를 EHMO법으로 구하였다. 이 형태의 안정도는 황원자와 벤젠고리 사이의 n-π 콘쥬게이션에 따른다는 것을 알았다. 또 염화벤젠술페닐의 가에탄올 분해반응을 연구하여 얻은 반응속도상수를 치환기 효과와 황원자의 d-궤도함수 기여로 논의하였다. 비선형 Hammett 그래프로 부터 쌍뿔형의 중간체를 제안할 수 있었다.

The preferred conformation of benzenesulfenyl chloride was determined by EHMO calculation. It was found that the stability was dictated by the n-π conjugation of S atom with the benzene ring. The ethanolysis reaction of benzenesulfenyl chlorides has been studied. The rate constants obtained have been discussed in terms of substituent effects and d-orbital participation of sulfur atom. From a non-linear Hammett plot, bipyramid type of intermediate has been suggested.

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15 - 18
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