Preparation and enantioseparation properties of chiral stationary phases derived from arylcarbamoylated β-cyclodextrin

Four chiral stationary phases were prepared by the immobilization of arylcarbarnoylated beta-cyclodextrin onto functionalized silica gel via a long covalent linkage. Silica gel was glycidoxy-functionalized, followed by amino-functionalization with 1,6-diaminohexane for further reaction to yield a long chain spacer. The structures of all compounds prepared were characterized by FT-IR, H-1 NMR, C-13 NMR, and elemental analysis. From the data of elemental analysis, the surface concentrations of the spacer and the derivatized beta-cyclodextrin on silica gel were determined, and the results showed that on average, of eight spacers on silica gel, only one was linked to beta-cyclodextrin derivative. The enantioseparation capability of the four prepared chiral columns was evaluated by high performance liquid chromatography. The chiral stationary phase that was prepared from phenylcarbamoylated beta-cyclodextrin showed the best enantioseparation capability towards a wide variety of racernic mixtures. The chiral stationary phase that was prepared frorn 3,5-dimethylphenylcarbmoylated beta-cyclodextrin showed good en anti oseparati on capability for pyrimidine derivatives. The chiral stationary phases that were prepared, respectively, from 1-naphthylcarbamoylated beta-cyclodextrin and 2-methoxyphenylcarbamoylated beta-cyclodextrin were less effective for enantioseparation.