Highly Accurate Quantitative Analysis Of Enantiomeric Mixtures from Spatially Frequency Encoded 1 H NMR Spectra

We propose an original concept to measure accurately enantiomeric excesses on proton NMR spectra, which combines high-resolution techniques based on a spatial encoding of the sample, with the use of optically active weakly orienting solvents. We show that it is possible to simulate accurately dipola...

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Bibliographic Details
Published in:Analytical chemistry (Washington) 2018-02, Vol.90 (3), p.1595-1600
Main Authors: Plainchont, Bertrand, Pitoux, Daisy, Cyrille, Mathieu, Giraud, Nicolas
Format: Article
Language:English
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Summary:We propose an original concept to measure accurately enantiomeric excesses on proton NMR spectra, which combines high-resolution techniques based on a spatial encoding of the sample, with the use of optically active weakly orienting solvents. We show that it is possible to simulate accurately dipolar edited spectra of enantiomers dissolved in a chiral liquid crystalline phase, and to use these simulations to calibrate integrations that can be measured on experimental data, in order to perform a quantitative chiral analysis. This approach is demonstrated on a chemical intermediate for which optical purity is an essential criterion. We find that there is a very good correlation between the experimental and calculated integration ratios extracted from G-SERF spectra, which paves the way to a general method of determination of enantiomeric excesses based on the observation of H nuclei.
ISSN:0003-2700
1520-6882
DOI:10.1021/acs.analchem.7b02411