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The resolution of some chiral compounds in reversed-phase high-performance liquid chromatography by means of β-cyclodextrin inclusion complexes

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Summary

β-Cyclodextrin is applied as the chiral component of the mobile phase in a systematic study of the resolution —into enantiomers — of mandelic acid and its derivatives by reversed-phase liquid chromatography. It is found that the stereoselectivity arising from inclusion in β-cyclodextrin molecules is significant (α=1.02÷1.05) only for the compounds showing at the asymmetric carbon atom the presence of first, an intact carboxylic group and second, a functional group capable of hydrogen bonding with the hydroxyl groups of β-cyclodextrin. Results are discussed in the light of the three-point attachment model of stereoselectivity as well as of the structure of the inclusion complexes.

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Dębowski, J., Sybilska, D. & Jurczak, J. The resolution of some chiral compounds in reversed-phase high-performance liquid chromatography by means of β-cyclodextrin inclusion complexes. Chromatographia 16, 198–200 (1982). https://doi.org/10.1007/BF02258899

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  • DOI: https://doi.org/10.1007/BF02258899

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