Quantum-chemical modeling of the mechanism for reaction of arenesulfonyl chlorides with α-amino acids

We have calculated the potential energy surface for arenesulfonylation reactions of a-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 N 2 mechanism. Hydration of glycine lowers the...

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Bibliographic Details
Published in:Theoretical and experimental chemistry 2011-03, Vol.47 (1), p.61-66
Main Authors: Kochetova, L. B., Kustova, T. P., Kalinina, N. V., Ishkulova, N. R., Lutsyuk, V. V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Summary:We have calculated the potential energy surface for arenesulfonylation reactions of a-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 N 2 mechanism. Hydration of glycine lowers the activation energy compared with the gas phase.
ISSN:0040-5760
1573-935X
DOI:10.1007/s11237-011-9186-x