2H and 13C NMR-Based Enantiodetection Using Polyacetylene versus Polypeptide Aligning Media: Versatile and Complementary Tools for Chemists

Abstract : In this work, the practical/analytical potential of an L-valinederived polyacetylene (PLA) lyotropic liquid crystal (LLC) is examined to spectrally discriminate enantiomers (racemic mixture) or enantiotopic directions of a large collection (23) of (pro)chiral model compounds (from rigid to flexible and polar to apolar ones), thus covering various important aspects of enantiomorphism. Experimental 2H-{1H} (deuterated analytes and at natural abundance level) and 13C-{1H} NMR results are discussed in terms of the difference of 2H-RQCs or 13C-RCSAs and compared to those obtained in polypeptide-type LLCs (PBLG). The analysis of the NMR results provides an overview of the enantiodifferentiation capabilities of PLA and gives useful/ practical hints for the chemist to select the most appropriate chiral oriented system. Astonishing NAD NMR results wereobtained in the case of one of the simplest, chiral alkanes, 3-methylhexane. From a theoretical viewpoint, the data collected highlight the key molecular factors involved in orientation/discrimination processes, as a basis for optimizing computationalprediction (molecular dynamics simulation), as well asdesigning novel helically chiral polymers as new enantiodiscriminating aligning media. In addition, a new, robust and efficient protocol to synthesize PLA and its enantiomer (PDA) on a large scale and with small polydispersities is proposed.
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https://hal.archives-ouvertes.fr/hal-02308749
Contributor : Philippe Lesot <>
Submitted on : Tuesday, October 8, 2019 - 4:53:59 PM
Last modification on : Saturday, October 26, 2019 - 1:44:18 AM

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Philippe Lesot, Philippe Berdagué, Abdelkrim Meddour, Markus Noll, Michael Reggelin. 2H and 13C NMR-Based Enantiodetection Using Polyacetylene versus Polypeptide Aligning Media: Versatile and Complementary Tools for Chemists. ChemPlusChem, Wiley, 2019, 84 (2), pp.144-153. ⟨10.1002/cplu.201800493⟩. ⟨hal-02308749⟩

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