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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GA203%2F09%2F1919" target="_blank" >GA203/09/1919: Vývoj metody stanovení konfigurace na chirálních centrech obsahujících atom síry, dusíku nebo fosforu pomocí NMR spektroskopie a ab initio výpočtů</a><br>

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2011

Kód důvěrnosti údajů

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

Název periodika

Tetrahedron Asymmetry

ISSN

0957-4166

e-ISSN

—

Svazek periodika

22

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

356-366

Kód UT WoS článku

000290074800016

EID výsledku v databázi Scopus

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