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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 35, Number 1
JKCSEZ 35(1)
February 20, 1991 

Kinetic Studies for the Reaction of p-Methylphenacyl Arenesulfonates with Pyridine under High Pressures

고압하에서 p-Methylphenacyl Arenesulfonate와 피리딘과의 반응메카니즘
Soo-Dong Yoh, Heon-Young Park, Jong-Hwan Park, Jung-Ui Hwang

여수동, 박현영, 박종환, 황정의
아세토니트릴 용매 중에서 p-methylphenacyl arenesulfonate와 피리딘의 반응을 1∼2000 bars 및 35∼55℃에서 전기전도도법으로 측정하였다. 반응속도는 온도와 압력의 증가에 따라 증가하였으며, 이탈기에 전자받개 치환기가 도입됨에 따라 증가하였다. 활성화엔탄피, 엔트로피 및 부피로부터 이 반응은 전반적으로 Sn2 반응으로 진행되나 압력이 증가함에 따라 C····O 결합분열이 더욱 진전된 dissociative Sn2 반응으로 진행됨을 알 수 있었다.

Kinetics of the reaction of p-methylphenacyl arenesulfonates with pyridine in acetonitrile were investigated by an electric conductivity method at 1∼2000 bars and 35∼55℃. The rates of these reactions were increased with raising pressures and temperatures. The activation enthalpy(△H≠), entropy(△S≠) and activation volume(△V≠) of the reaction were obtained with the rate constants. Activation volume and entropy were both negative valued, and activation enthalpy was positive. The acteivation parameters (△V≠ and △S≠) were decreased with increasing pressure. From all of the above results, it was found that this reaction proceeds on the SN2 in which C‥‥O bond breaking is more advanced as pressure increases.

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