Abstract
AbstractChiral recognition mechanism of tris(4‐trimethylsilylphenylcarbamate) (1) and tris(5‐fluoro‐2‐methylphenylcarbamate) (2) of cellulose which are effective chiral stationary phases for HPLC were investigated using NMR spectroscopy. The phenylcarbamate derivatives are soluble in chloroform and exhibited chiral discrimination for several enantiomers in NMR as well as in HPLC. Especially, enantiomers of 2,2'‐dihydroxy‐1,1'‐binaphthyl (4) were distinctly discriminated by 2 in 1H and 13C NMR spectroscopies. The binding geometry and dynamics between 2 and the enantiomers of 4 were investigated on the basis of spin‐lattice relaxation time, 1H NMR titrations, and intermolecular NOEs in the presence of 2. These NMR data were fully consistent with the chromatographic elution order. On the basis of these results, combined with molecular modeling, the chiral discrimination mechanism is proposed.
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