Title

Evaluation of chiral discrimination of highly negatively charged enantiomers by quaternary ammonium β‐cyclodextrin using 1H NMR

Document Type

Article

Date of Publication

10-7-2005

Publication Title

Chirality

First Page

570

Last Page

576

Abstract

The positively charged quaternary ammonium cyclodextrin, QA‐β‐CD, was previously used as a chiral selector to achieve baseline resolution of two of the dianionic enantiomers of disodium 3‐(p‐isothiocyanatophenoxy)‐3‐(p‐isothiocyanatophenyl)propane‐1,2‐disulfate by capillary electrophoresis. The basis of the chiral discrimination between QA‐β‐CD and the enantiomers was investigated by 1H NMR spectroscopy. COSY and NOESY spectra were used to infer the role that molecular interactions and the stereocenters have upon association of QA‐β‐CD with the enantiomers. A parallel two‐step complexation model is used to rationalize the NMR and the chiral discrimination observed during separation of the enantiomers. © 2005 Wiley‐Liss, Inc. Chirality 17:570–576, 2005.

DOI

https://doi.org/10.1002/chir.20209

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