Issue 7, 2015

Vinyl sulfone building blocks in covalently reversible reactions with thiols

Abstract

In the present study we use quantum-chemical calculations to investigate how the reactivity of vinyl sulfone-based compounds can be modified from an irreversible to a reversible reaction with thiols. Based on the predictions from theory, an array of nine different vinyl sulfones with systematically varying substitution pattern was synthesized and their crystal structures were determined. Subsequent Hirshfeld surface analyses employing the principle of electrostatic complementarity aid the understanding of the crystal packing of the synthesized compounds. Reactivity studies against the nucleophile 2-phenylethanethiol mirror the properties predicted by the quantum-chemical computations in solution.

Graphical abstract: Vinyl sulfone building blocks in covalently reversible reactions with thiols

Supplementary files

Article information

Article type
Paper
Submitted
10 Feb 2015
Accepted
27 May 2015
First published
17 Jun 2015
This article is Open Access
Creative Commons BY-NC license

New J. Chem., 2015,39, 5841-5853

Author version available

Vinyl sulfone building blocks in covalently reversible reactions with thiols

T. H. Schneider, M. Rieger, K. Ansorg, A. N. Sobolev, T. Schirmeister, B. Engels and S. Grabowsky, New J. Chem., 2015, 39, 5841 DOI: 10.1039/C5NJ00368G

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