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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 41, Number 1
JKCSEZ 41(1)
February 20, 1997 

 
Title
Kinetic Studies on Nucleophilic Substitution Reaction of Phenacyl Halides with Pyridines in MeOH-MeCN Mixtures

메탄올-아세토니트릴 혼합용매계에서 할로겐화 펜아실과 피리딘유도체와의 친핵성 치환반응에 대한 속도론적 연구
Author
In Sun Koo, Kiyull Yang, Jong Keun Park, Ikchoon Lee

구인순,양기열,박종근,이익춘
Keywords
Abstract
25℃와 35℃에서 메탄올-아세토니트릴 혼합용매계에 대한 할로겐화 펜아실과 피리딘 치환체와의 친핵성치환반응을 속도론적으로 연구하였다. 전이상태 파라미터인 ΔH≠와 ΔS≠ 및 Bronsted β값으로 보아 Sn2 반응 메카니즘을 예상할 수 있었고, 이탈기 변화에 따른 QM 모형의 적용으로 이들 반응의 전이상태 역시 생성물 닮은 구조임을 알 수 있었다.

Kinetic studies on nucleophilic substitution reaction of phenacyl bromide and phenacyl chloride with pyridines were conducted at 25℃ and 35℃ in methanol-acetonitrile solvents mixtures. It was shown that the reaction proceeds via an SN2 reaction mechanism based on the transition state parameters, ΔH≠ and ΔS≠ and Bro nsted β values. Quantum mechanical model predicted a product-like transition state, where bond-formation is much more progressed than bond breaking, upon changing the leaving group to that with a better leaving ability.

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46 - 51
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