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Title:Preparation and evaluation of several new pi-basic chiral stationary phases
Author(s):Deming, Kris Carl
Doctoral Committee Chair(s):Pirkle, William H.
Department / Program:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Analytical
Chemistry, Organic
Abstract:Several new chiral stationary phases (CSPs) derived from $\alpha$-arylalkylamines and N-arylamino acids are evaluated based on their chromatographic performance. These new chiral stationary phases are useful for separation of the enantiomers of N-(3,5-dinitrobenzoyl) derivatized $\alpha$- and $\beta$-amino esters and amides, amines, amino alcohols, alcohols and $\alpha$-amino phosphonates. These new CSPs are also very useful for separation of the enantiomers of N- and O-(3,5-dinitroanilido) derivatives of amines and alcohols and 3,5-dinitroanilide derivatives of chiral acids. A comparison is made between the CSP derived from N-(1-naphthyl)leucine and the commercially available CSP derived from N-(2-naphthyl)alanine based on the magnitude of chromatographic separation factors on the two stationary phases. Proton NMR studies and an X-ray crystal structure are discussed and provide additional support for the proposed chiral recognition model between N-(3,5-dinitrobenzoyl)amino acid derivatives and N-arylamino acid derived CSPs.
Issue Date:1989
Rights Information:Copyright 1989 Deming, Kris Carl
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9010844
OCLC Identifier:(UMI)AAI9010844

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