Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography |
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| Authors: | Ren-Qi Wang Teng-Teng Ong Weihua Tang Siu-Choon Ng |
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| Affiliation: | 1. Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, 16 Nanyang Drive, Singapore 637722, Singapore;2. Key Laboratory of Soft Chemistry and Functional Materials (Ministry of Education of China), Nanjing University of Science and Technology, Nanjing 210094, People''s Republic of China |
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| Abstract: | Two covalently bonded cationic β-CD chiral stationary phases (CSPs) prepared by graft polymerization of 6A-(3-vinylimidazolium)-6-deoxyperphenylcarbamate-β-cyclodextrin chloride or 6A-(N,N-allylmethylammonium)-6-deoxyperphenylcarbamoyl-β-cyclodextrin chloride onto silica gel were successfully applied in high-performance liquid chromatography (HPLC). Their enantioseparation capability was examined with 12 racemic pharmaceuticals and 6 carboxylic acids. The results indicated that imidazolium-containing β-CD CSP afforded more favorable enantioseparations than that containing ammonium moiety under normal-phase HPLC. The cationic moiety on β-CD CSPs could form strong hydrogen bonding with analytes in normal-phase liquid chromatography (NPLC) to enhance the analytes’ retention and enantioseparations. In reversed-phase liquid chromatography (RPLC), the analytes exhibited their maximum retention when the pH of mobile phase was close to their pKa value. Inclusion complexation with CD cavity and columbic/ionic interactions with cationic substituent on the CD rim would afford accentuated retention and enantioseparations of the analytes. |
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| Keywords: | β-cyclodextrin Chiral stationary phase High-performance liquid chromatography Enantioseparation Electrostatic force Ionic liquid |
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