Synthesis and enantioseparation characteristics of a novel mono-6-deoxy-(2,4-dihydroxybenzimide)-β-cyclodextrin as a chiral stationary phase in high-performance liquid chromatography

A novel chiral selector mono-6-deoxy-(2,4-dihydroxybenzimide)-β-CD (MDHB-β-CD) in which the derivatized group and the cavity of CD is linked by CH2–NC group, was successfully prepared, and the structural characteristics were determined by FT-IR, 1H and 13C NMR, MALDITOF-MS and element analysis. The corresponding stationary phase (CSP) was used in HPLC and the enantioseparation performance was investigated using chiral 1-phenyl-2-nitroethanol derivatives as test samples in the reverse-phase mode composed of methanol/water and acetonitrile/TEAA. Better separation abilities and excellent enantioselectivities (α > 1.26, RS > 1.73) were obtained on MDHB-β-CD CSP for these chiral compounds in the methanol/water mobile phase.