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The determination of sulfoxide configuration in six-membered rings using NMR specroscopy and DFT calculations
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SYSNO ASEP 0360400 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title The determination of sulfoxide configuration in six-membered rings using NMR specroscopy and DFT calculations Author(s) Dračínský, Martin (UOCHB-X) RID, ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Slavětínská, Lenka (UOCHB-X) RID
Janků, J. (CZ)
Buděšínský, Miloš (UOCHB-X) RID, ORCIDNumber of authors 5 Source Title Tetrahedron Asymmetry. - : Elsevier - ISSN 0957-4166
Roč. 22, č. 3 (2011), s. 356-366Number of pages 11 s. Language eng - English Country GB - United Kingdom Keywords NMR ; calculation of NMR parameters ; sulfoxides ; configuration Subject RIV CC - Organic Chemistry R&D Projects GA203/09/1919 GA ČR - Czech Science Foundation (CSF) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000290074800016 DOI 10.1016/j.tetasy.2011.02.001 Annotation Cyclic six-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. The oxidation was followed by NMR spectra and the 1H and 13C NMR data were collected. The geometries of all of the compounds were optimized using the DFT B3LYP/6-31G** method and the 13C and 1H NMR chemical shifts were calculated for geometry-optimized structures with the DFT B3LYP/6-31++G** method. The calculated 13C NMR chemical shifts induced by oxidation (Dd values) are in very good agreement with the experimental data and can be used to determine the oxidation state of the sulfur atom (–S–, –SO–, –SO2–). The characteristic differences of the induced oxidation chemical shifts of carbon atoms at the a- and b-position to sulfur were successfully used for distinguishing between the diastereoisomeric sulfoxides. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2012
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