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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 34, Number 3
JKCSEZ 34(3)
June 20, 1990 

Kinetic Studies on the Nucleophilic Reactions of Substituted Benzylnitrates with Anilines in CH3CN-CH3OH

아세토니트릴-메탄올 혼합용매계에서 질산벤질과 아닐린의 친핵성 치환반응
Chang-Kook Sohn, Wang Ki Kim, Soo-Jeong Lee, Kiyull Yang

손창국, 김왕기, 이수정, 양기열
50-100% CH3CN-CH3OH 혼합용매계에서 파라-치환된 질산벤질과 아닐린과의 친핵성 치환반응에 대한 2차 속도상수를 전기전도도법으로 구하였다. 속도자료를 이용하여 Hammett ρN과 ρC값, Brφnsted β값 및 용매화 파라미터 계수들을 구하였으며 이들을 PES및 양자역학 모형에 적용하여 구조 변화를 논의하였다. 연구 결과 결합형성보다 결합절단이 비교적 많이 진행된 상태에서 치환기 변화에 따라 결합절단의 진척이 결합형성을 촉진하는 동시적 SN2 반응메카니즘으로 진행됨을 알았다.

Kinetic studies on the nucleophilic reactions of p-substituted benzylnitrates with substituted anilines have been conductometically carried out in 50-100% CH3CN-CH3OH mixtures. From the kinetic data, Hammett ρC and ρN values, Brφnsted β values, and solvatochromic coefficients were determined in order to examine the transition state variations caused by changes in substituents and solvent properties. It is concluded that the reaction proceeds via a synchronous SN2 mechanism in which bond formation is more advanced than bond cleavage.

227 - 231
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