Exploring the interactions between chiral molecules and molecular micelles with NMR spectroscopy

CHED 311

Stephanie A. Kingsbury, skingsbury@carthage.edu and Kevin F. Morris, kmorris@carthage.edu. Department of Chemistry, Carthage College, 2001 Alford Park Drive, Kenosha, WI 53140
Molecular micelles are used in electrokinetic chromatography to analyze mixtures of chiral molecules. In this technique, enantiomers are separated based upon their differential interactions with the chiral atoms on the headgroups of the macromolecule. The goal of this project was to use NMR spectroscopy to characterize the interactions between four chiral molecules and the molecular micelle poly(sodium N-undecanoyl-L-leucylleucinate). NMR diffusion experiments were used to probe the relationship between the analyte enantiomers' free energies of binding to the molecular micelle and chiral selectivities from electrokinetic chromatography. Two-dimensional NOESY experiments identified each enantiomer's site of chiral binding and allowed a structural model of the analyte: molecular micelle complexes to be developed.