An NMR Study of Chiral Recognition Relevant to the Liquid Chromatographic Separation of Enantiomers by a Cellulose Derivative

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.