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

✍ Scribed by Qinfeng Liu; L.M. Viranga Tillekeratne; Yong-Wah Kim; Jon R. Kirchhoff; Richard A. Hudson

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
125 KB
Volume
17
Category
Article
ISSN
0899-0042

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✦ Synopsis

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 ^1^H 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.

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1H NMR chiral analysis of benzhydrylamin
1H NMR chiral analysis of benzhydrylamine derivatives using β-cyclodextrin. Solution geometry of host-guest complexes as determined by 1D NOE and ROESY experiments
✍ J. Redondo; J. Frigola; A. Torrens; P. Lupón 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 459 KB

## Abstract The ^1^H NMR chiral analysis of a series of benzhydrylamine derivatives was accomplished by means of β‐cyclodextrin as chiral resolving agent, forming the corresponding inclusion complexes in aqueous solution. NOE and ROESY experiments were used in order to establish the most probable h