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Capillary electrophoretic separation of binaphthyl enantiomers with two polymeric chiral surfactants: 1 H‐nuclear magnetic resonance and fluorescence spectroscopy study
Author(s) -
Yarabe H. Hyacinthe,
Rugutt Joseph K.,
McCarroll Matthew E.,
Warner Isiah M.
Publication year - 2000
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/1522-2683(20000601)21:10<2025::aid-elps2025>3.0.co;2-p
Subject(s) - enantiomer , chemistry , titration , capillary electrophoresis , micellar electrokinetic chromatography , fluorescence spectroscopy , nuclear magnetic resonance spectroscopy , fluorescence , proton nmr , two dimensional nuclear magnetic resonance spectroscopy , analytical chemistry (journal) , chromatography , organic chemistry , stereochemistry , physics , quantum mechanics
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 1 H‐nuclear magnetic resonance ( 1 H‐NMR) titrations and fluorescence spectroscopy, respectively. The 1 H‐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 1 H‐NMR data.