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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 

Nucleophilic Substitution at a Carbonyl Carbon Atom (Ⅶ). Kinetic Studies on the Sovolysis of 2-Thenoyl Chloride in Binary Mixtures of Acetone-Water and Ethanol-Water

카르보닐 탄소원자의 친핵성 치환반응 (제7보). 물-에탄올 및 물-아세톤 혼합용매속에서 2-염화테노일의 가용매 분해반응
Jin-Eon Sohn, Sang-Kee Yoon, Ikchoon Lee

손진언, 윤상기, 이익춘
여러가지 조성의 물-아세톤 및 물-에탄올 혼합용매 속에서 2-염화테노일의 가용매 분해반응속도를 20 ∼ 40℃에서 측정하여 활성화 파라미터를 계산하고 Winstein 그림표의 기울기와 혼합용매조성에 따른 속도 상수 상수의 변화를 검토하였다. 실험결과 혼합용매의 물함량이 증가할 수록 Sn1 반응성이 강하게 나타남을 보았다. 그러나 염화벤조일의 가용매 분해반응속도 보다는 느림을 알았다.

The rates of solvolysis for 2-thenoyl chloride have been measured in aqueous acetone and aqueous ethanol at various temperatures ranging from 20 to 40℃. The activation parameters and the Grundwald-Winstein's slope are determined by the analysis of solvolysis rates. The results indicated that the reaction rates of solvolysis are considerably slower than those of the reaction for benzoyl chloride due to the electron donating effect of thiophene nucleus. The results also showed that the reaction proceeds with the SN1 mechanism in water-rich solvents whereas the SN2 character increases with the decrease of water content, and overall reaction is subject to entropy control.

333 - 339
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