31P NMR parameters may facilitate the stereochemical analysis of phosphorus-containing compounds
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
35121491
DOI
10.1016/j.jmr.2022.107149
PII: S1090-7807(22)00007-6
Knihovny.cz E-resources
- MeSH
- Circular Dichroism MeSH
- Phosphorus * MeSH
- Magnetic Resonance Spectroscopy MeSH
- Molecular Conformation MeSH
- Stereoisomerism MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Phosphorus * MeSH
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.
Department of Inorganic Chemistry Faculty of Science Charles University 116 28 Prague Czech Republic
Department of Organic Chemistry Faculty of Science Charles University 116 28 Prague Czech Republic
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