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Title:Investigations of molecular recognition processes
Author(s):Burke, John Andrew, III
Doctoral Committee Chair(s):Pirkle, William H.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Chemistry, Pharmaceutical
Abstract:The use of chiral stationary phases (CSPs) for the separation of enantiomers is commonplace. A variety of $\alpha$-alkyl and $\alpha$-aryl substituted $\alpha$-amino phosphonates were prepared. The ability of several CSPs to separate the enantiomers of N-(3,5-dinitrobenzoyl) derivatives of $\alpha$-alkyl and $\alpha$-aryl substituted $\alpha$-amino phosphonates was investigated. Using the chromatographic structure-activity relationships, chiral recognition models were proposed. For one class of CSP, the chiral recognition model has been further supported using spectroscopic and chromatographic evidence. Two $\alpha$-amino phosphonate derived CSPs were prepared and their ability to separate the enantiomers of a variety of analytes was studied. The mechanistic implications of analyte-CSP spatial complementarity were investigated. Two new CSPs derived from the 3,5-dinitrobenzamide of an $\alpha$-amino acid were prepared and evaluated.
Issue Date:1992
Type:Text
Language:English
URI:http://hdl.handle.net/2142/22300
Rights Information:Copyright 1992 Burke, John Andrew, III
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9236407
OCLC Identifier:(UMI)AAI9236407


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