期刊
JOURNAL OF SEPARATION SCIENCE
卷 39, 期 21, 页码 4136-4146出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jssc.201600609
关键词
Cyclodextrins; Enantioseparation; Ionic liquids; Stationary phases
资金
- National Natural Science Foundation of China [21172020]
A simple procedure for the synthesis of three new oxazolinyl-substituted beta-cyclodextrins (6-deoxy-6-R-(-)-4-phenyl-4,5-dihydrooxazolinyl-beta-cyclodextrin, 6-deoxy-6-S-(-)-4-phenyl-4,5-dihydrooxazolinyl-beta-cyclodextrin, and 6-deoxy-6-S-(-)-(4-pyridin-1-ium-4-methyl-benzenesulphonate)-4,5-dihy-drooxazolinyl-beta-cyclodextrin) and their covalent bonding to silica are reported. The ability of these chiral stationary phase columns for separating compounds is also presented and discussed. Twenty-eight compounds were examined in the polar-organic mobile phase mode, and 11 beta-nitroethanols were tested in the reversed-phase mode. Excellent enantioseparations were achieved for most of the analytes, even for several challenging compounds. The rigid and flexible structures of mono-substituted chiral groups and the fragments around the rim of the beta-cyclodextrin cavity played an important role in the separation process. Factors such as pi-pi stacking, dipole-dipole interactions, ion-pairing, and steric hindrance effects were found to affect the chromatographic performance. Moreover, the buffer composition, and percentages of organic modifiers in the mobile phase, were investigated and compared. The mechanisms involved in the separation were postulated based on the chromatographic data.
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