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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 23, Number 6
JKCSEZ 23(6)
December 20, 1979 

Nucleophilic Substitution at a Carbonyl Carbon Atom (Ⅹ). Nucleophilic Substitution Reactions of N,N-Disubstituted Carbamoyl Chlorides

카르보닐탄소원자의 친핵성 치환반응 (제10보). N,N-이치환 염화카르바모일의 친핵성 치환반응
Shi Choon Kim, Ho Bong Song, Ikchoon Lee

김시준, 송호봉, 이익춘
염화 N,N-이메틸 및 N,N-이에틸카르바모일의 가용매분해반응과 할라이드 교환(Cl-, Br-, I-)반응, 및 염화 N,N-이페닐카르바모일의 가용매분해반응을 속도론적으로 연구하였다. 속도자료와 MO결과로부터 (1) 이 알킬화합물들은 Sn2 메카니즘으로, 이페닐화합물은 Sn1 메카니즘으로 반응함을 알았고, (2) 염화이온교환에서는 결합절단이 중요한 반면, Br- 및 I- 교환반응에서는 결합 형성이 중요함을 알 수 있었다.

Kinetic studies have been carried out on solvolyses and halide exchanges (Cl-, Br-, I-) of N,N-dimethyl-, N,N-diethylcarbamoyl chlorides, and solvolyses of N,N-diphenylcarbamoyl chloride. Kinetic results together with simple MO analysis indicated that: (a) N,N-dialkylcarbamoyl chlorides reacted via the SN2 mechanism, while N,N-diphenylcarbamoylchloride reacted via the SN1 mechanism; (b) in chloride exchanges, the bond-breaking appeared to be important, whereas in bromide and iodide exchanges, the bond-formation was shown to be important.

368 - 373
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