Schneider, Thomas H.; Rieger, Max; Ansorg, Kay; Sobolev, Alexandre N.; Schirmeister, Tanja; Engels, Bernd; Grabowsky, Simon (2015). Vinyl sulfone building blocks in covalently reversible reactions with thiols. New journal of chemistry, 39(7), pp. 5841-5853. Royal Society of Chemistry 10.1039/C5NJ00368G
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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.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Grabowsky, Simon |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
1144-0546 |
Publisher: |
Royal Society of Chemistry |
Language: |
English |
Submitter: |
Simon Grabowsky |
Date Deposited: |
06 Feb 2020 11:40 |
Last Modified: |
05 Dec 2022 15:35 |
Publisher DOI: |
10.1039/C5NJ00368G |
BORIS DOI: |
10.7892/boris.138465 |
URI: |
https://boris.unibe.ch/id/eprint/138465 |
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