Diphenylethanediamine derivatives as chiral selectors: III. Comparison of four new diastereomeric chiral stationary phases prepared by addition of mono-3,5-dinitrobenzoyldiphenylethanediamine derivatives to optically pure epoxy silica

• Published in: Journal of Chromatography A 1994-04, Vol.666 (1), p.41-53
• Main Authors: Uray, G., Maier, N.M., Lindner, W.
• Format: Article
• Language: English
• Subjects: Analytical chemistry; Chemistry; Chromatographic methods and physical methods associated with chromatography; Exact sciences and technology; Other chromatographic methods
• ISSN: 0021-9673
• DOI: 10.1016/0021-9673(94)80369-2

The synthesis and normal-phase HPLC evaluation of four diastereomeric chiral stationary phases (CSPs) based on mono-3,5-dinitrobenzoylated 1,2-diphenylethane-1,2-diamine (DPEDA) as chiral selector is described. Addition of the free amino function to an optically pure epoxide bound to silica resulted in CSPs having an amino alcohol function additionally to the π-acidic dinitrobenzoylamido group. Efficient separation of the 1-naphthyl derivatized enantiomers of aromatic amines, alcohols and carboxylic acids could be accomplished. The main difference in enantioseparation capabilities is found between ( R, R)- or ( S, S)-DPEDA derived CSPs I and II and the meso-DPEDA derived CSP III and IV, the latter being only more effective in the case of increased steric hindrance of the analytes.