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α-Substitution Effects on the Ease of S→N-Acyl Transfer in Aminothioesters

• 2013
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Publication Information
Authors Bahaa El-Dien M. El-Gendy, Ebrahim H. Ghazvini Zadeh, Ania C. Sotuyo, Girinath G. Pillai andAlan R. Katritzky
Keywords Not Available
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publication.type International
Paper Link Open Link
Supplementary Materials Not Available
Abstract
In S-acylcysteines and homocysteines, the efficacy and rate of S→N-acyl transfer (5 and 6 cyclic TSs) vary with the size of S-acyl group. Conformational and quantum chemical calculations indicate that the spatial distance, b(N-C), between the terminal amine and the thioester carbon is shortened by α-C(O)X (X = OH, OMe, NH2) substituents.