Jump to main content
Jump to site search

Issue 7, 2015
Previous Article Next Article

Vinyl sulfone building blocks in covalently reversible reactions with thiols

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 10 Feb 2015, accepted on 27 May 2015 and first published on 17 Jun 2015


Article type: Paper
DOI: 10.1039/C5NJ00368G
Author version
available:
Download author version (PDF)
New J. Chem., 2015,39, 5841-5853
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    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

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements