The determination of sulfoxide configuration in six-membered rings using NMR specroscopy and DFT calculations

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F11%3A00360400" target="_blank" >RIV/61388963:_____/11:00360400 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/j.tetasy.2011.02.001" target="_blank" >http://dx.doi.org/10.1016/j.tetasy.2011.02.001</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tetasy.2011.02.001" target="_blank" >10.1016/j.tetasy.2011.02.001</a>

Result language

angličtina

Original language name

The determination of sulfoxide configuration in six-membered rings using NMR specroscopy and DFT calculations

Original language description

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 ofcarbon atoms at the a- and b-position to sulfur were successfully used for distinguishing between the diastereoisomeric sulfoxides.

Czech name

—

Czech description

—

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

—

Project

<a href="/en/project/GA203%2F09%2F1919" target="_blank" >GA203/09/1919: Development of methods for configuration determination at chiral sulfur, nitrogen or phosphorus atom using NMR spectroscopy and ab initio calculations</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2011

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Tetrahedron Asymmetry

ISSN

0957-4166

e-ISSN

—

Volume of the periodical

22

Issue of the periodical within the volume

3

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

356-366

UT code for WoS article

000290074800016

EID of the result in the Scopus database

—