Hexakis(2,3-di-O-benzoyl)-R-cyclodextrin and hexakis(2,3,6-tri-O-benzoyl)-R-cyclodextrin have been employed as chiral solvating agents (CSAs) for the NMR determination of the enantiomeric composition of derivatives of chiral amines, amino alcohols, alcohols, carboxyl acids, and amino acids bearing a 3,5-dinitrophenyl moiety. The conformational features of the two cyclodextrins have been carefully analyzed by NMR spectroscopy, and the origin of the symmetry change (C6 f C3), detected by NMR for hexakis(2,3-di-O-benzoyl)-R-cyclodextrin in CDCl3, has been clarified.

A new stereochemical model from NMR for benzoylated cyclodextrins, promising new chiral solvating agents for the chiral analysis of 3,5-dinitrophenyl derivatives

UCCELLO BARRETTA, GLORIA;BALZANO, FEDERICA;MENICAGLI, RITA;IULIANO, ANNA;SALVADORI, PIERO
1997

Abstract

Hexakis(2,3-di-O-benzoyl)-R-cyclodextrin and hexakis(2,3,6-tri-O-benzoyl)-R-cyclodextrin have been employed as chiral solvating agents (CSAs) for the NMR determination of the enantiomeric composition of derivatives of chiral amines, amino alcohols, alcohols, carboxyl acids, and amino acids bearing a 3,5-dinitrophenyl moiety. The conformational features of the two cyclodextrins have been carefully analyzed by NMR spectroscopy, and the origin of the symmetry change (C6 f C3), detected by NMR for hexakis(2,3-di-O-benzoyl)-R-cyclodextrin in CDCl3, has been clarified.
UCCELLO BARRETTA, Gloria; Cuzzola, A.; Balzano, Federica; Menicagli, Rita; Iuliano, Anna; Salvadori, Piero
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/175010
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