Separation of 2-naphthol atropisomers on cyclofructan-based chiral stationary phases |
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| Authors: | Lillian A Frink Alain Berthod Qing-Long Xu Hongyin Gao Laszló Kurti |
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| Institution: | 1. Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, Texas, USA;2. Institute of Analytical Sciences, CNRS, University of Lyon 1, Villeurbanne, France;3. Department of Chemistry, Bioscience Research Collaborative, Rice University, Houston, Texas, USA |
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| Abstract: | A set of fifteen 2-naphthol-derived atropisomers were evaluated on three different cyclofructan-based chiral stationary phases (CSP). The cyclofructan CSPs were a dimethylphenyl-derivatized cyclofructan 7 (CF7-DMP), a isopropyl (CF6-P) and a R-naphthylethyl cyclofructan 6 (CF6-RN) derivative, all bonded to 5-µm spherical fully porous silica particles packed into three 25?cm?×?4.6?mm columns (commercially available as Larihc columns). The 15 atropisomers were analyzed in the normal-phase mode with heptane/alcohol mobile phases. The CF7-DMP column was the most effective partially or fully separating 14 of the 15 compounds (93%). All 15 compounds could be separated by at least one cyclofructan column. Five compounds could be partially or fully separated by all three CSPs. The effect of ethanol, 2-propanol and butanol as 5 and 10% v/v polar modifiers in heptane was studied. A prototype 15?cm?×?4.6?mm column packed with superficially porous 2.7?µm CF6-P bonded particles was tested with the same set of compounds and a standard HPLC system. The increased efficiency and solvent saving were significant. |
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| Keywords: | Atropisomer separation cyclofructan selectors 2-naphthol phenyl derivatives superficially porous particles |
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