Vinyl sulfone building blocks in covalently reversible reactions with thiols

T.H. Schneider, M. Rieger, K. Ansorg, Alexandre Sobolev, T. Schirmeister, B. Engels, Simon Grabowsky

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10 Citations (Scopus)

Abstract

© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015. 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.
Original languageEnglish
Pages (from-to)5841-5853
JournalNew Journal of Chemistry
Volume39
Issue number7
Early online date17 Jun 2015
DOIs
Publication statusPublished - 1 Jul 2015

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