Journal
MOLECULES
Volume 23, Issue 7, Pages -Publisher
MDPI
DOI: 10.3390/molecules23071785
Keywords
enantiomers; Pirkle's alcohol; TFAE; qNMR; mandelonitrile; CSA; chirality; chiral solvating agent
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The discrimination of enantiomers of mandelonitrile by means of 1D C-13 NMR and with the aid of the chiral solvating agent (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol (TFAE) is presented. H-1 NMR fails for this specific compound because proton signals either overlap with the signals of the chiral solvating agent or do not show separation between the (S)-enantiomer and the (R)-enantiomer. The C-13 NMR method is validated by preparing artificial mixtures of the (R)-enantiomer and the racemate, and it is shown that with only 4 mg of mandelonitrile a detection limit of the minor enantiomer of 0.5% is obtained, corresponding to an enantiomeric excess value of 99%. Furthermore, the method shows high linearity, and has a small relative standard deviation of only 0.3% for the minor enantiomer when the relative abundance of this enantiomer is 20%. Therefore, the C-13 NMR method is highly suitable for quantitative enantiodiscrimination. It is discussed that C-13 NMR is preferred over H-1 NMR in many situations, not only in molecules with more than one chiral center, resulting in complex mixtures of many stereoisomers, but also in the case of molecules with overlapping multiplets in the H-1 NMR spectrum, and in the case of molecules with many quaternary carbon atoms, and therefore less abundant protons.
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