Nucleophilic Displacement at Sulfer Center (IV). Solvolysis of p-Substituted Benzenesulfonyl Chlorides in Acetonitrile-Water Mixtures

황의 친핵치환 반응 (제4보). 아세토니트릴-물 혼합용매에서의 파라치환염 벤젠술포닐의 가용매분해

  • Wang Ki Kim (Department of Science Education, Chonnam National University) ;
  • Ikchoon Lee (Department of Chemistry, Inha University)
  • Published : 1974.02.28

Abstract

The solvolysis of p-substituted benzenesulfonyl chlorides $(substituents:p-H, p-Br, p-NO_2, p-OCH_3)$ in acetonitrile-water mixtures below 50 % of water content has been studied kinetically. Results show that Hammett plots give concaved curves but the mechanism is predominantly $S_N2$ and water acts both as nucleophile and general-base.

물함량 50% 이하의 아세토니트릴-물 혼합용매내에서의 염화벤젠술포닐의 $p-H, p-NO_2, p-Br, p-OCH_3$, 치환체들의 가용매분해를 반응속도론적으로 연구한 결과 Hammett 도시는 concave한 곡선들이나 $S-N2$성격이 압도적이었으며 물은 친핵제 뿐만 아니라 general base로도 작용하고 있음을 알았다.

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