13C nuclear spin‐spin relaxation times (T2Cs) of enantiomers in the presence of column packing material and solvents for chiral discrimination HPLC

Abstract

To elucidate chiral recognition difference between pairs of enantiomers which interacted with a cellulosic stationary phase of chiral discrimination high performance liquid chromatography (HPLC), 13C NMR spectroscopy was applied for enantiomers of 1-phenylethanol, 1-indanol, 1,2,3,4,-tetrahydro-1-naphthol, glutethimide, and Tröger's base. Their 13C nuclear spin-spin relaxation times (T2Cs) and spectra were obtained in deuterated HPLC solvents in the presence of column packing material made of cellulose tris(4-methylbenzoate) coated on silica gel. The first-eluted enantiomers on the HPLC showed longer T2Cs and stronger signal intensities of 13C NMR spectra than the second-eluted enantiomers. These results indicated that the chiral recognition difference of enantiomers was observed by their T2Cs and intensities of 13C NMR spectra. The T2C difference was found to reflect the retention order of enantiomers on the chiral HPLC column. © 1996 Wiley-Liss, Inc.