Chiral discrimination of aliphatic amines and amino alcohols using NMR spectroscopy

Wenzel, Thomas J.; Rollo, Ryan D.; Clark, Rebecca L.

doi:10.1002/mrc.2855

Cited by 10 publications

(1 citation statement)

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“…Other worth mentioning achievements are the first successful enantiomeric discrimination of chiral alkanes [269,270], of sibutramine enantiomers by capillary electrophoresis [271], of aliphatic amines and amino alcohols [272], the chiral discrimination of β-telluride carboxylic acids [273], of secondary alcohols and carboxylic acids [274], the application of roof shape amines as chiral solvating agents for discrimination of optically active acids [275], the recognition of enantiomers of dipeptide derivatives with two chiral centers [276].…”

Section: Chemical Methods For Chiral Discrimination Via Nmr Spectroscopymentioning

confidence: 99%

Chiral discrimination in nuclear magnetic resonance spectroscopy

Lazzeretti

2017

J. Phys.: Condens. Matter

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Chirality is a fundamental property of molecules whose spatial symmetry is characterized by the absence of improper rotations, making them not superimposable to their mirror image. Chiral molecules constitute the elementary building blocks of living species and one enantiomer is favoured in general (e.g. L-aminoacids and D-sugars pervade terrestrial homochiral biochemistry) because most chemical reactions producing natural substances are enantioselective. Since the effect of chiral chemicals and drugs on living beings can be markedly different between enantiomers, the quest for practical spectroscopical methods to scrutinize chirality is an issue of great importance and interest. Nuclear magnetic resonance (NMR) is a topmost analytical technique, but spectrometers currently used are 'blind' to chirality, i.e. unable to discriminate the two mirror-image forms of a chiral molecule, because, in the absence of a chiral solvent, the spectral parameters, chemical shifts and spin-spin coupling constants are identical for enantiomers. Therefore, the development of new procedures for routine chiral recognition would offer basic support to scientists. However, in the presence of magnetic fields, a distinction between true and false chirality is mandatory. The former epitomizes natural optical activity, which is rationalized by a time-even pseudoscalar, i.e. the trace of a second-rank tensor, the mixed electric dipole/magnetic dipole polarizability. The Faraday effect, magnetic circular dichroism and magnetic optical activity are instead related to a time-odd axial vector. The present review summarizes recent theoretical and experimental efforts to discriminate enantiomers via NMR spectroscopy, with the focus on the deep connection between chirality and symmetry properties under the combined set of fundamental discrete operations, namely charge conjugation, parity (space inversion) and time (motion) reversal.

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