Quantum-chemical modeling of the mechanism for reaction of arenesulfonyl chlorides with [alpha]-amino acids

We have calculated the potential energy surface for arenesulfonylation reactions of [alpha]-amino acids and glycine hydrates. We have shown that all the reactions occur via a complicated route, with varying angle of attack by the nucleophile according to an [S.sub.N]2 mechanism. Hydration of glycine...

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Published inTheoretical and experimental chemistry Vol. 47; no. 1; p. 61
Main Authors Kochetova, L.B, Kustova, T.P, Kalinina, N.V, Ishkulova, N.R, Lutsyuk, V.V
Format Journal Article
LanguageEnglish
Published Springer 01.03.2011
Subjects
Chlorides
Dichloropropane
Glycine
Hydrates
Hydrolysis
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Summary:We have calculated the potential energy surface for arenesulfonylation reactions of [alpha]-amino acids and glycine hydrates. We have shown that all the reactions occur via a complicated route, with varying angle of attack by the nucleophile according to an [S.sub.N]2 mechanism. Hydration of glycine lowers the activation energy compared with the gas phase. Key words: aminolysis, [alpha]-amino acids, arenesulfonyl chlorides, mechanism, quantum-chemical modeling.
ISSN:0040-5760
1573-935X