Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F14%3A10272022" target="_blank" >RIV/00216208:11310/14:10272022 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/14:00429646

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.tet.2014.04.047" target="_blank" >http://dx.doi.org/10.1016/j.tet.2014.04.047</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2014.04.047" target="_blank" >10.1016/j.tet.2014.04.047</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts

Popis výsledku v původním jazyce

The six-membered saturated heterocycles-4-tert-butyl-1 -methylpiperidine, 4-tert-butyl-1methylphosphine, 4-tert-butyl-tetrahydro-2H-thiopyran, and 4-tert-butyl-tetrahydro-2H-selenopyran were prepared as suitable model compounds with well-defined geometryfor an NMR study of their oxidation products. The corresponding epimeric N-oxides, phosphinoxides, sulfoxides, and selenoxides were obtained by standard chemical preparation and also by in situ oxidation with meta-chloroperbenzoic acid directly in the NMR tube. The experimental H-1 and C-13 chemical shifts were compared with corresponding calculated data obtained by CIAO approach with DFT, MP2, and HF methods and various basis sets. The correlation of experimental versus calculated data showed the possibility to determine the stereochemistiy of the epimeric oxidation products using fast DFT B3LYP/6-31G* method for both geometry optimization and NMR chemical shifts calculation.

Název v anglickém jazyce

Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts

Popis výsledku anglicky

The six-membered saturated heterocycles-4-tert-butyl-1 -methylpiperidine, 4-tert-butyl-1methylphosphine, 4-tert-butyl-tetrahydro-2H-thiopyran, and 4-tert-butyl-tetrahydro-2H-selenopyran were prepared as suitable model compounds with well-defined geometryfor an NMR study of their oxidation products. The corresponding epimeric N-oxides, phosphinoxides, sulfoxides, and selenoxides were obtained by standard chemical preparation and also by in situ oxidation with meta-chloroperbenzoic acid directly in the NMR tube. The experimental H-1 and C-13 chemical shifts were compared with corresponding calculated data obtained by CIAO approach with DFT, MP2, and HF methods and various basis sets. The correlation of experimental versus calculated data showed the possibility to determine the stereochemistiy of the epimeric oxidation products using fast DFT B3LYP/6-31G* method for both geometry optimization and NMR chemical shifts calculation.

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

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2014

Kód důvěrnosti údajů

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

Název periodika

Tetrahedron

ISSN

0040-4020

e-ISSN

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Svazek periodika

70

Číslo periodika v rámci svazku

25

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

16

Strana od-do

3871-3886

Kód UT WoS článku

000336699900006

EID výsledku v databázi Scopus

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