Journal of the Chemical Society. Perkin transactions II p. 1473 - 1478 (1988)
Update date:2022-09-26
Topics:
Baltes, Michel
Cazaux, Louis
Gorrichon, Liliane
Maroni, Pierre
Tisnes, Pierre
t-Butyl N-arylsulphinamoylacetates are hydrolysed in aqueous basic media by an elimination mechanism. It takes place on the conjugate base of the substrate resulting from a fast deprotonation of the activated methylene group. This elimination is first order (E1cB) for compounds where strong electron-withdrawing groups substitute the aromatic ring. For substitution by weaker electron-withdrawing or -donating groups, the elimination is second order, and needs the presence of general acid catalysis. For t-butyl N-(2-hydroxyphenyl)sulphinamoylisobutyrate where this mechanism of elimination is impossible, a BAc2 attack by hydroxide ion at the sulphur atom takes place. From these mechanisms and the results of complexation of zinc(II) cations by sulphinamoylacetates, a possible scheme for the irreversible inactivation of the title zinc metalloenzyme is proposed.
View MoreLaohekou Jinghong Chemical Co.,Ltd
Contact:+86-0710-3702747
Address:163.East，Huagong Road，Laohekou
Contact:86-791-86629460
Address:1-6F, 118 Xinzhou road, Nanchang, Jiangxi, China
SJZ Chenghui Chemical Co., Ltd.
Contact:86-311-87713916
Address:no.368 youyi north avenue
website:http://www.angchenchem.com
Contact:+86-510-88302099 82327577
Address:Rm. 404/405, Floor 4th, No. 983 FengXiang Road, Wuxi, China
SHANGHAI RC CHEMICALS CO.,LTD.
website:http://www.rcc.net.cn
Contact:+86-21-50322175
Address:Rm1415 Yinqiao Masion No.58 Jinxin Road Pudong Shanghai China
Doi:10.1021/jm201045m
(2011)Doi:10.1021/ja01528a039
(1959)Doi:10.1016/S0040-4039(00)83940-4
(1986)Doi:10.1016/S0040-4039(00)96818-7
(1987)Doi:10.1039/b906266a
(2009)Doi:10.1016/S0040-4020(01)86649-7
(1988)
