High-performance liquid chromatography of diamine enantiomers as Schiff bases on a chiral stationary phase

A high-performance liquid chromatographic method for the enantiomeric analysis of chiral 1,2-diamines is described. By derivatization with benzaldehyde, aliphatic and aromatic 1,2-diamines were converted into Schiff base derivatives. Separation of the enantiomeric derivatives was performed on a comm...

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Bibliographic Details
Published inJournal of Chromatography A Vol. 664; no. 2; pp. 169 - 176
Main Authors Duchateau, A.L.L., Guns, J.J., Kubben, R.G.R., van Tilburg, A.F.P.
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier B.V 01.04.1994
Elsevier
Subjects
Analytical chemistry
Chemistry
Chromatographic methods and physical methods associated with chromatography
Exact sciences and technology
Other chromatographic methods
Capacity factor
Peak resolution
Enantioselectivity
Benzaldehyde
HPLC chromatography
Chiral stationary phase
Derivatization
Experimental study
Organic carbamate
Schiff base
Diamine
Analytical reagent
Cellulose derivatives
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Summary:A high-performance liquid chromatographic method for the enantiomeric analysis of chiral 1,2-diamines is described. By derivatization with benzaldehyde, aliphatic and aromatic 1,2-diamines were converted into Schiff base derivatives. Separation of the enantiomeric derivatives was performed on a commercially available cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase. To investigate the effect of the reagent structure on enantioseparation, a series of twenty ring-substituted benzaldehydes were reacted with an aliphatic and an aromatic diamine. The influence of the type of substituent of the benzaldehyde reagent on the enantioselectivity obtained for Schiff base derivatives is discussed.
ISSN:0021-9673
DOI:10.1016/0021-9673(94)87004-7