Proton NMR assignments for R,S-1,1′-binaphthol (BN) and R,S-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (BNDHP) interacting with bile salt micelles

• Published in: Magnetic resonance in chemistry 2007-01, Vol.45 (1), p.72-75
• Main Authors: Eckenroad, Kyle W., Thompson, Laura E., Strein, Timothy G., Rovnyak, David
• Format: Article
• Language: English
• Subjects: bile salt micelles; binaphthol; capillary electrophoresis; micellar electrokinetic capillary electrophoresis; NMR
• ISSN: 0749-1581; 1097-458X
• DOI: 10.1002/mrc.1916

We report proton chemical shifts for two model chiral analytes that are commonly used in the study of micellar electrokinetic capillary chromatography (MEKC), R,S‐1,1′‐binaphthol (1, BN) and R,S‐1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate (2, BNDHP), in the absence and presence of monomers and micelles of sodium cholate and sodium deoxycholate. The analytes undergo fast exchange in and out of the micelles, which perturbs the analytes' chemical shifts, and which we use to resolve some resonances that are degenerate at both 300 and 600 MHz. Although BN and BNDHP are simple molecules, the proton assignments are only unambiguously established with the aid of the exchange with micelles, an attractive alternative to other methodologies such as the use of paramagnetic shift reagents which may also cause spectral distortions. We rely also upon 2D‐NOE spectra of samples in the presence of micelles to perform these assignments. Recently published assignments, which were based upon 2D‐COSY spectroscopy, appear to be in error and are corrected here. Finally, we note that these shifts are information‐rich reporters on the nature of the interactions of these model analytes with the micelles. Copyright © 2006 John Wiley & Sons, Ltd.