Determination of the enantiomeric composition of α-methylbenzylamine by the formation of a transient diastereoisomeric excited complex with 2,2′-dihydroxy-1,1′-binaphthalene

Abstract

A novel method for the determination of enantiomeric purity is described. It is based on the appearance of a fluorescent emission from a diastereoisomeric complex formed between a fluorescent acid in its excited state and a non-fluorescent base. A linear relationship between the intensity of this emission and the enantiomeric composition of the non-fluorescent base has been shown, and this has been used successfully to determine the enantiomeric composition of two unknown samples of the base. The limit of quantitation of one enantiomer in the presence of another has been shown to be 5%, and the method has been shown to measure a difference of 5% in enantiomeric composition.