The determination of sulfoxide configuration in five-membered rings using NMR spectroscopy and DFT calculations

0368029 - ÚOCHB 2012 RIV GB eng J - Článek v odborném periodiku
Dračínský, Martin - Pohl, Radek - Slavětínská, Lenka - Hřebabecký, Hubert - Buděšínský, Miloš
The determination of sulfoxide configuration in five-membered rings using NMR spectroscopy and DFT calculations.
Tetrahedron Asymmetry. Roč. 22, 18/19 (2011), s. 1797-1808. ISSN 0957-4166
Grant CEP: GA ČR GA203/09/1919
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: NMR spectroscopy * DFT calculations * sulfoxides
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.652, rok: 2011

Cyclic five-membered ring sulfoxides and sulfones were prepared by a stepwise in situ oxidation of the corresponding sulfides with meta-chloroperbenzoic acid in an NMR tube. DFT calculated 13C chemical shifts induced by oxidation were in very good agreement with the experimental data and could be used to determine the oxidation state of the sulfur atom and to distinguish between the diastereoisomeric sulfoxides and allowed configuration determination.
Trvalý link: http://hdl.handle.net/11104/0202502