Benzoylated and Benzylated Cyclodextrins: a New Class of Chiral Solvating Agents for the Enantiomeric Purity Determination of 3,5-Dinitrophenyl Derivatives by NMR

Benzoylated and benzylated cyclodextrins give rise to non-equivalence in the 1H-NMR spectra of racemates of 3,5-dinitrophenyl derivatives of chiral amines, amino alcohols, alcohols, carboxylic acids and amino acids in CDCl3 solution, suggesting their potential use as CDCl3-soluble cyclodextrinic chiral solvating agents (CSAs) in NMR spectroscopy. Cyclodextrins bearing aromatic substituents at the primary or secondary sites only are more efficient CSAs compared to exhaustively substituted ones. NMR investigations based on NOE measurements or complexation shift determinations strongly suggest non-inclusive interaction mechanisms for these selector/selectand system