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.
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