Preparation and Enantioseparation Properties of Chiral Stationary Phases Derived from Arylcarbamoylated β‐Cyclodextrin

Four chiral stationary phases were prepared by the immobilization of arylcarbamoylated β‐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, 1H NMR, 13C NMR, and elemental analysis. From the data of elemental analysis, the surface concentrations of the spacer and the derivatized β‐cyclodextrin on silica gel were determined, and the results showed that on average, of eight spacers on silica gel, only one was linked to β‐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 β‐cyclodextrin showed the best enantioseparation capability towards a wide variety of racemic mixtures. The chiral stationary phase that was prepared from 3,5‐dimethylphenylcarbmoylated β‐cyclodextrin showed good enantioseparation capability for pyrimidine derivatives. The chiral stationary phases that were prepared, respectively, from 1‐naphthylcarbamoylated β‐cyclodextrin and 2‐methoxyphenylcarbamoylated β‐cyclodextrin were less effective for enantioseparation.