High-performance liquid chromatography using β-cyclodextrin bonded phases was examined for the enantiomeric separation of racemic nicotine and 19 racemic nicotine analogues. Ten pairs of enantiomers were separated by this technique. This represents the first reported facile and direct separation of these racemates. Effects of pH, mobile phase composition, and structural features of the substrates (i.e., position and size of substituents, presence of pyrrolidine ring or hydrogen bonding functionalities, basicity) on the enantioselectivity are examined. Various structural aspects of the compounds were related to retention to the cyclodextrln-modlfied support and to the enantiomeric separations observed. Implications of this work to host-guest complexation are discussed. © 1988, American Chemical Society. All rights reserved.
J. I. Seeman et al., "Enantiomeric Resolution And Chiral Recognition Of Racemic Nicotine And Nicotine Analogues By Β-cyclodextrin Complexation: Structure-enantiomeric Resolution Relationships In Host-guest Interactions," Analytical Chemistry, vol. 60, no. 19, pp. 2120 - 2127, American Chemical Society, Oct 1988.
The definitive version is available at https://doi.org/10.1021/ac00170a027
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01 Oct 1988