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 Morewebsite:http://www.weichichem.com
Contact:+8613912949432
Address:Fine Chemical Industrial Base,Wujiang town,He County,Anhui China.
Tianjin Jiuri New Materials Co., Ltd.
Contact:+86-22-58889220
Address:C-5/6, Vison Hill, No.1 Gonghua Road, Huayuan Hi-tech Park, Tianjin, China.
Contact:+1 (647) 918 5848
Address:2343 BRIMLEY RD., Suite 250
Beijing Century Richap Chemistry Co.,Ltd
Contact:+86- 010-64455497
Address:Guannan County, Lianyungang City, Jiangsu Province, China
Contact:+49-4101-3053-0
Address:Waldhofstrasse 14 ,25474 Ellerbek Germany
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)
