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RESEARCH PRODUCT
Vinyl sulfone building blocks in covalently reversible reactions with thiols
Thomas SchneiderMax RiegerSimon GrabowskySimon GrabowskyKay AnsorgBernd EngelsTanja SchirmeisterAlexandre N. Sobolevsubject
010405 organic chemistryChemistrytechnology industry and agricultureGeneral ChemistryCrystal structureVinyl sulfone010402 general chemistry01 natural sciencesCombinatorial chemistryCatalysisReversible reaction0104 chemical sciencesCrystalNucleophileCovalent bondPolymer chemistryMaterials ChemistryReactivity (chemistry)description
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-01-01 | New Journal of Chemistry |