E. Yashima, C. Yamamoto, Y. Okamoto
May 1, 1996
Citations
0
Influential Citations
160
Citations
Quality indicators
Journal
Journal of the American Chemical Society
Abstract
Chromatographic enantioseparation of 1,1‘-bi-2-naphthol (2) and its mono- and di-O-methylated derivatives (3a, 3b), 2,2‘-dihydroxy-6,6‘-dimethylbiphenyl (4), and 10,10‘-dihydroxy-9,9‘-biphenanthryl (5) has been performed on cellulose tris(5-fluoro-2-methylphenylcarbamate) (1) as a chiral stationary phase for high-performance liquid chromatography (HPLC). The complete base-line separation of 2 and 4 was achieved with the elution order of enantiomers such that the (R)-isomers eluted first followed by the (S)-isomers. The resolution of 5 and the O-methylated 3 was difficult on 1. The cellulose derivative 1 dissolved in chloroform also exhibited a chiral discrimination for 2 and 4 in 1H and 13C NMR spectroscopies as well as in HPLC. The hydroxy and some aromatic protons and carbon resonances of 2 and 4 were clearly separated into a pair of peaks due to enantiomers in the presence of 1. The binding geometry and dynamics between 1 and the enantiomers of 2 were investigated on the basis of spin−lattice relaxatio...