31P NMR parameters may facilitate the stereochemical analysis of phosphorus-containing compounds

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F22%3A00553163" target="_blank" >RIV/61388963:_____/22:00553163 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/22:10443949

Výsledek na webu

<a href="https://doi.org/10.1016/j.jmr.2022.107149" target="_blank" >https://doi.org/10.1016/j.jmr.2022.107149</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.jmr.2022.107149" target="_blank" >10.1016/j.jmr.2022.107149</a>

Jazyk výsledku

angličtina

Název v původním jazyce

31P NMR parameters may facilitate the stereochemical analysis of phosphorus-containing compounds

Popis výsledku v původním jazyce

Conventional Nuclear Magnetic Resonance (NMR) analysis relies on H-H/C-H interactions. However, these interactions are sometimes insufficient for an accurate and precise NMR analysis. In this study, we show that 31P NMR parameters can provide critical structural insights into the stereochemistry of phosphorus-containing compounds. For this purpose, we prepared a set of model phosphorus-based proline derivatives, separated diastereoisomers, and determined their absolute configuration by single-crystal X-ray diffraction. After supplementing these results by electronic circular dichroism (ECD) spectroscopy, we combined experimental data and DFT calculations from our model compounds to perform a detailed conformational analysis, thereby determining their relative configuration. Overall, our findings establish an experimental paradigm for combining 31P NMR spectroscopy with other optical methods to facilitate the stereochemical analysis of phosphorus-containing compounds.

Název v anglickém jazyce

31P NMR parameters may facilitate the stereochemical analysis of phosphorus-containing compounds

Popis výsledku anglicky

Conventional Nuclear Magnetic Resonance (NMR) analysis relies on H-H/C-H interactions. However, these interactions are sometimes insufficient for an accurate and precise NMR analysis. In this study, we show that 31P NMR parameters can provide critical structural insights into the stereochemistry of phosphorus-containing compounds. For this purpose, we prepared a set of model phosphorus-based proline derivatives, separated diastereoisomers, and determined their absolute configuration by single-crystal X-ray diffraction. After supplementing these results by electronic circular dichroism (ECD) spectroscopy, we combined experimental data and DFT calculations from our model compounds to perform a detailed conformational analysis, thereby determining their relative configuration. Overall, our findings establish an experimental paradigm for combining 31P NMR spectroscopy with other optical methods to facilitate the stereochemical analysis of phosphorus-containing compounds.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10406 - Analytical chemistry

Projekt

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

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2022

Kód důvěrnosti údajů

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

Název periodika

Journal of Magnetic Resonance

ISSN

1090-7807

e-ISSN

1096-0856

Svazek periodika

336

Číslo periodika v rámci svazku

March

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

107149

Kód UT WoS článku

000783431600002

EID výsledku v databázi Scopus

2-s2.0-85123858544