NMR-aided differentiation of enantiomers: Signal enantioresolution

[Display omitted] •The concept and importance of NMR signal enantioresolution is described.•The enantioresolution quotient E for its measurement is introduced.•E allows more reliable analyses of enantiodifferentiation data than previous methods.•Using E opens up possibilities for analyzing data comi...

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Bibliographic Details
Published in:Analytica chimica acta 2015-05, Vol.876, p.63-70
Main Authors: Pérez-Trujillo, Míriam, Parella, Teodor, Kuhn, Lars T.
Format: Article
Language:English
Subjects:
Algorithms
Chiral complexing agents
Enantiodifferentiation
Enantioresolution
Enantioresolution quotient
Magnetic Resonance Spectroscopy - methods
NMR spectroscopy
Stereoisomerism
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Summary:[Display omitted] •The concept and importance of NMR signal enantioresolution is described.•The enantioresolution quotient E for its measurement is introduced.•E allows more reliable analyses of enantiodifferentiation data than previous methods.•Using E opens up possibilities for analyzing data coming from different NMR methods. NMR-aided enantiodiscrimination using chiral auxiliaries (CAs) is a recognized method for differentiating enantiomers and for measuring enantiomeric ratios (er). Up to the present, the study, optimization, and comparison of such methods have been performed based on the enantiodifferentiation of NMR signals via analyzing non-equivalent chemical-shift values (ΔΔδ) of the diastereoisomeric species formed. However, a poor and non-reliable comparison of results is often obtained via the analysis of ΔΔδ exclusively. In here, the concept of enantioresolution of an individual NMR signal and its importance for NMR-aided enantiodifferentiation studies is introduced and discussed. In addition, the enantioresolution quotient, E, is proposed as the parameter to describe its quantification. Complementary to measuring ΔΔδ, the experimental determination of E allows a more reliable interpretation of the results and opens up new possibilities for the study of enantiodifferentiation data derived from novel NMR experiments, setup improvements or new CAs. Finally, the different relationships between signal enantiodifferentiation, signal enantioresolution, and other main experimental issues of enantiodifferentiation experiments are addressed.
ISSN:0003-2670
1873-4324
DOI:10.1016/j.aca.2015.02.069