Current time in Korea 13:27 Oct 15 (Tue) Year 2019 KCS KCS Publications
KCS Publications
My Journal Log In Register
HOME > Search > Browsing(JKCS) > Archives

Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 35, Number 2
JKCSEZ 35(2)
April 20, 1991 

 
Title
Hydrolysis Mechanism of Phenyl N-phenylbenzthioimidate Derivatives

Phenyl N-phenylbenzthioimidate 유도체들의 가수분해 반응메카니즘
Author
Nack-Do Sung, Young-Jae Kim, Ki-Sung Kwon, Tae-Rin Kim

성낙도, 김영재, 권기성, 김태린
Keywords
Abstract
25℃의 dioxane-수용액 25%(v/v) 중에서 이탈기인 S-phenyl group의 para 위치에 작용기가 치환된 phenyl N-phenylbenzthioimidate 유도체들의 가수분해 반응을 속도론적으로 연구하였다. 반응속도식, 치환기 효과, 공통이온 효과, 용매효과, 온도의 영향 및 생성물 분석결과는 본 반응이 pH 9.0 이하에서, 이온-쌍(IP) 중간체를 거치는 "SN1(IP)"메카니즘으로 반응이 일어나지만, pH 11.0 이상에서는 전이상태를 경유하는 "회합Sn2" 메카니즘으로 반응이 일어나며 pH 9.0 ~ 11.0 사이에서는 이들 두 반응이 경쟁적으로 일어남을 제안하였다.

The rate of hydrolysis of phenyl N-phenylbenzthioimidate derivatives which are para substituted on the S-phenyl ring as leaving group have been investigated kinetically in aqueous dioxane 25%(v/v) at 25℃. Rate equation, substituent effect, common ion effect, solvent effect, salt effect, temperature effect and product analysis suggest that the SN1(IP) mechanism proceeds via ion-pair(IP) intermediate below pH 9.0 and associative SN2 mechanism proceeds via the transition state above pH 11.0, and from pH 9.0 to pH 11.0 these two reactions occur competitively.

Page
182 - 178
Full Text
PDF