Evaluation Of A Chiral Crown Ether LC Column For The Separation Of Racemic Amines
Abstract
Enantiomeric resolution of more than fifty racemic primary amines can be achieved on a column that utilizes a crown ether as a chiral selector. The racemic solute is solubilized in an acidic solvent, forming an ammonium ion from the primary amine functional group. An interaction between the lone pair electrons on the oxygens of the crown ether and the positive charge of the ammonium group leads to the formation of an inclusion complex. Due to the chirality of the crown ether there is stereoselective interaction resulting in enantiomeric separation. Excellent resolution is possible for amino acids, amino alcohols, amino esters and amines. Compounds are separated that were poorly resolved by conventional ligand exchange columns and by other means. © 1991, Taylor & Francis Group, LLC. All rights reserved.
Recommended Citation
M. Hilton and D. W. Armstrong, "Evaluation Of A Chiral Crown Ether LC Column For The Separation Of Racemic Amines," Journal of Liquid Chromatography, vol. 14, no. 1, pp. 9 - 28, Taylor and Francis Group; Taylor and Francis, Jan 1991.
The definitive version is available at https://doi.org/10.1080/01483919108049594
Department(s)
Chemistry
International Standard Serial Number (ISSN)
0148-3919
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2023 Taylor and Francis Group; Taylor and Francis, All rights reserved.
Publication Date
01 Jan 1991
