An NMR Study of Chiral Recognition Relevant to the Liquid Chromatographic Separation of Enantiomers by a Cellulose Derivative
- 1 March 1994
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 23 (3) , 579-582
- https://doi.org/10.1246/cl.1994.579
Abstract
Chiral discrimination of enantiomers by cellulose tris(4-trimethylsilylphenylcarbamate) (CTSP) was studied by 1H NMR spectroscopy. The 1H NMR signals of trans-stilbene oxide and 2-butanol were enantiomerically separated into two sets of peaks in the presence of CTSP in CDCl3. The competition experiment with acetone suggests that trans-stilbene oxide may be adsorbed on the NH proton of carbamate residues of CTSP. Chemical shift non-equivalence in enantiotopic methyl groups of 2-propanol was observed in the presence of CTSP.Keywords
This publication has 10 references indexed in Scilit:
- Enantiomeric excess analysis of sesquiterpene precursors through proton decoupled deuterium NMR in cholesteric lyotropic liquid crystalTetrahedron: Asymmetry, 1993
- α,α,α′,α′‐Tetraaryl‐1,3‐dioxolane‐4,5‐dimethanols (TADDOLs) for Resolutions of Alcohols and as Chiral Solvating Agents in NMR SpectroscopyHelvetica Chimica Acta, 1992
- A spectroscopic study of the interaction of (D)- and (L)-N-(3,5-dinitrobenzoyl)valine methyl ester with n-butylamide of (S)-2-[(phenylcarbamoyl)oxy]propionic acid: direct evidence for a chromatographic chiral recognition rationaleJournal of the American Chemical Society, 1990
- Proton NMR studies of tris(phenanthroline) metal complexes bound to oligonucleotides: characterization of binding modesBiochemistry, 1990
- Considerations of chiral recognition relevant to the liquid chromatography separation of enantiomersChemical Reviews, 1989
- Intermolecular proton[proton] nuclear Overhauser effects in diastereomeric complexes: support for a chromatographically derived chiral recognition modelJournal of the American Chemical Society, 1986
- Chiral separation of heterocyclic drugs by HPLC: solute-stationary phase base-pair interactionsJournal of the American Chemical Society, 1986
- Chromatographic resolutionJournal of Chromatography A, 1986
- The determination of absolute configuration using nuclear magnetic resonance techniquesProgress in Nuclear Magnetic Resonance Spectroscopy, 1982
- Chemical shift nonequivalence in prochiral groupsChemical Reviews, 1975