The unique power of Liquid Crystal NMR (LXNMR) in obtaining information about the conformational equilibrium of small solutes dissolved in orienting media can be effectively used to study chirality-related phenomena. In this work we have been able, for the first time in our knowledge, to fully resolve the two different conformational distributions for the R and S enantiomers of a case test molecule (the chiral flexible 4FMBOH: 4-F-α-methyl benzyl alcohol), dissolved in a typical chiral non-racemic aligning solvent, made of PBLG (poly- γ -benzyl-L-glutamate, a helical chiral polypeptide) co-dissolved in CDCl3. The two enantiomers show significant differences in their conformational behaviors, due to the different solute–solvent orientational molecular interactions experienced by the R and S species. In our opinion, fundamental studies of this kind could pave the way for a better understanding of chirality-dependent molecular interactions, often involved in a number of important chemical processes (concerning pharmaceuticals, biochemistry, advanced materials, etc.)

Assessing the chirality-dependent conformational distribution of small flexible opposite enantiomers dissolved in weakly ordering enantiopure media by means of liquid crystal NMR techniques

Salvino R. A.;De Luca G.;Celebre G.
2021-01-01

Abstract

The unique power of Liquid Crystal NMR (LXNMR) in obtaining information about the conformational equilibrium of small solutes dissolved in orienting media can be effectively used to study chirality-related phenomena. In this work we have been able, for the first time in our knowledge, to fully resolve the two different conformational distributions for the R and S enantiomers of a case test molecule (the chiral flexible 4FMBOH: 4-F-α-methyl benzyl alcohol), dissolved in a typical chiral non-racemic aligning solvent, made of PBLG (poly- γ -benzyl-L-glutamate, a helical chiral polypeptide) co-dissolved in CDCl3. The two enantiomers show significant differences in their conformational behaviors, due to the different solute–solvent orientational molecular interactions experienced by the R and S species. In our opinion, fundamental studies of this kind could pave the way for a better understanding of chirality-dependent molecular interactions, often involved in a number of important chemical processes (concerning pharmaceuticals, biochemistry, advanced materials, etc.)
2021
Chirality-dependent Conformational Distributions of Enantiomers
Chirality-dependent Orientational Order Parameters of Enantiomers
Liquid Crystal NMR Techniques
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/325812
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