Vinyl sulfone building blocks in covalently reversible reactions with thiols
Publisher DOI
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.
Date Issued
2015
Publication Type
Article
Subject(s)
Language(s)
en
Author(s)
Schneider, Thomas H. | |
Rieger, Max | |
Ansorg, Kay | |
Sobolev, Alexandre N. | |
Schirmeister, Tanja | |
Engels, Bernd |
Additional Credits
Journal
New journal of chemistry
Publisher
Royal Society of Chemistry
ISSN
1144-0546
Access(Rights)
restricted