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https://hdl.handle.net/2142/22300
Description
Title
Investigations of molecular recognition processes
Author(s)
Burke, John Andrew, III
Issue Date
1992
Doctoral Committee Chair(s)
Pirkle, William H.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Chemistry, Pharmaceutical
Language
eng
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.
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