Analysis of the13C NMR Spectra of Molecules, Chiral by Isotopic Substitution, Dissolved in a Chiral Oriented Environment: Towards the Absolute Assignment of the pro-R/pro-S Character of Enantiotopic Ligands in Prochiral Molecules - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2004

Analysis of the13C NMR Spectra of Molecules, Chiral by Isotopic Substitution, Dissolved in a Chiral Oriented Environment: Towards the Absolute Assignment of the pro-R/pro-S Character of Enantiotopic Ligands in Prochiral Molecules

Résumé

We examined and discuss the proton- and deuterium-decoupled carbon-13 1D spectrum of a molecule, chiral by virtue of the isotopic substitu-tion, dissolved in a chiral oriented medium which simultaneously exhibits chiral discrimination, enantiomeric en-richment and isotope effect. Using the 1-deutero-(2’,3’,4’,5’,6’-pentadeutero-phenyl)phenylmethanol orientationally ordered in a chiral nematic liquid crystal as illustrative example, we point out three important features. First, we demonstrate that the absolute assign-ment of the pro-R/pro-S character may be derived from the absolute configu-ration of the isotopically chiral analogue. Second, we report evidence that isotopic effect on 13C chemical shift anisotropy is negligible in a weakly ori-enting solvent. Third, we definitely es-tablish that the molecular orientation of prochiral Cs symmetry molecules and their parent compounds that are chiral by virtue of the isotopic substitu-tion is the same.

Dates et versions

hal-02310803 , version 1 (10-10-2019)

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Philippe Lesot, Olivier Lafon, Jacques Courtieu, Philippe Berdagué. Analysis of the13C NMR Spectra of Molecules, Chiral by Isotopic Substitution, Dissolved in a Chiral Oriented Environment: Towards the Absolute Assignment of the pro-R/pro-S Character of Enantiotopic Ligands in Prochiral Molecules. Chemistry - A European Journal, 2004, 10 (15), pp.3741-3746. ⟨10.1002/chem.200400065⟩. ⟨hal-02310803⟩
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