A rational approach to the design of highly effective chiral stationary phases for the liquid chromatographic separation of enantiomers.
The design and rationale of some novel chiral stationary phases (CSPs) are discussed with respect to methods for determining enantiomeric purity, absolute configuration and for obtaining enantiomerically pure materials by liquid chromatography. The commercially-available dinitrobenzoylamino CSP type 1 is discussed with respect to the chiral recognition mechanisms which may operate in the resolution of some polycyclic and heterocyclic aromatic molecules and some benzodiazepines. N-Acyl alpha-arylalkylamines are also employed as models to formulate mechanisms for the chiral properties of type 1 CSPs in terms of enantiomeric stacking of the most stable conformations in solution. The properties of new types of 'reciprocal' CSPs are discussed and illustrated by enantiomeric separation of some amino acid and amino phosphoric acid derivatives, and by the separation of the following enantiomeric drugs as their 3,5-dinitrobenzoyl derivatives: metoprolol, oxoprenolol, ephedrine and alprenolol.
Pirkle
W H
WH
School of Chemical Sciences, University of Illinois, 1209 W. California Street, Urbana, IL 61801, USA.
Hyun
M H
MH
Tsipouras
A
A
Hamper
B C
BC
Banks
B
B