Capillary electrophoretic separation of binaphthyl enantiomers with two polymeric chiral surfactants:1H-nuclear magnetic resonance and fluorescence spectroscopy study

Autor: Matthew E. McCarroll, H. Hyacinthe Yarabe, Isiah M. Warner, Joseph K. Rugutt
Rok vydání: 2000
Předmět:
Zdroj: Electrophoresis. 21:2025-2032
ISSN: 1522-2683
0173-0835
DOI: 10.1002/1522-2683(20000601)21:10<2025::aid-elps2025>3.0.co;2-p
Popis: The use of the water-soluble polymeric chiral surfactants (PCS), sodium N-undecanoyl-L-valinate (poly-L-SUV) and sodium undecanoyl-L-isoleucinate (poly-L-SUI) as buffer additives in electrokinetic chromatography (EKC) afforded the separation of racemic mixtures of 2,2'-dihydroxy-1,1'-binaphthyl (BOH) and 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (BNP). The apparent binding constants of the PCS to the enantiomers of BNP and BOH were obtained through 1H-nuclear magnetic resonance (1H-NMR) titrations and fluorescence spectroscopy, respectively. The 1H-NMR titration studies show that the BNP enantiomers are localized in the hydrophobic micellar pockets of PCS and form complexes of a 1:1 stoichiometry. The binding constants of PCS of BOH were determined from a Benesi-Hildebrand treatment of the fluorescence data. The EKC data corroborate those of the binding constants, supporting the formation of inclusion complexes. A model rationalizing the chiral discrimination of the enantiomers of BNP is proposed based on the intermolecular interactions observed in 1H-NMR data.
Databáze: OpenAIRE
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