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

0553163 - ÚOCHB 2023 RIV US eng J - Journal Article
Tichotová, Markéta - Ešnerová, A. - Tučková, Lucie - Bednárová, Lucie - Císařová, I. - Baszczyňski, Ondřej - Procházková, Eliška
31P NMR parameters may facilitate the stereochemical analysis of phosphorus-containing compounds.
Journal of Magnetic Resonance. Roč. 336, March (2022), č. článku 107149. ISSN 1090-7807. E-ISSN 1096-0856
R&D Projects: GA ČR(CZ) GA21-23014S
Institutional support: RVO:61388963
Keywords : circular dichroism spectroscopy * nuclear magnetic resonance spectroscopy * single crystals
OECD category: Analytical chemistry
Impact factor: 2.2, year: 2022
Method of publishing: Limited access
https://doi.org/10.1016/j.jmr.2022.107149

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.
Permanent Link: http://hdl.handle.net/11104/0328166


Research data: CCDC, CCDC