Regular Article
Enantioselective chromatography of alkyl derivatives of 5-ethyl-5-phenyl-2-thiobarbituric acid studied by semiempirical AM1 method
Krzysztof Zborowski,
Grzegorz Żuchowski,
Corresponding Author
Krzysztof Zborowski
Faculty of Chemistry, Jagiellonian University, Kraków, Poland
Faculty of Chemistry, Jagiellonian University, 3 Ingardena Str., 30-060 Kraków, PolandSearch for more papers by this authorGrzegorz Żuchowski
Department of Organic Chemistry, College of Medicine, Jagiellonian University, Kraków, Poland
Search for more papers by this authorKrzysztof Zborowski,
Grzegorz Żuchowski,
Corresponding Author
Krzysztof Zborowski
Faculty of Chemistry, Jagiellonian University, Kraków, Poland
Faculty of Chemistry, Jagiellonian University, 3 Ingardena Str., 30-060 Kraków, PolandSearch for more papers by this authorGrzegorz Żuchowski
Department of Organic Chemistry, College of Medicine, Jagiellonian University, Kraków, Poland
Search for more papers by this authorAbstract
Complexation of alkyl derivatives of 5-ethyl-5-phenyl-2-thiobarbituric acid (2-thiophenobarbital) enantiomers by β-cyclodextrin was investigated by the AM1 method. The inclusion complexes of β-cyclodextrin with neutral and anionic forms of these enantiomers have been modeled and energetically optimized. The chiral discrimination of enantiomers was analyzed in terms of differences in the interaction energies. The calculated interaction energies between each enantiomer of the investigated 2-thiobarbiturates and β-cyclodextrin confirm the ability of β-cyclodextrin to act as a mobile phase additive in reversed-phase HPLC to separate enantiomers by liquid chromatography and rationalize their order of elution. Chirality 14:632–637, 2002. © 2002 Wiley-Liss, Inc.
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