Mechanistic Aspects of Enantioselective Complexation
Murray, Patrick Gerard
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https://hdl.handle.net/2142/72296
Description
Title
Mechanistic Aspects of Enantioselective Complexation
Author(s)
Murray, Patrick Gerard
Issue Date
1994
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, Analytical
Chemistry, Organic
Abstract
The effect of differential penetration ("intercalation") of enantiomeric analytes between the strands of synthetic, brush-type liquid chromatographic chiral stationary phases (CSPs) has been investigated. The design and evaluation of a new family of $\pi$-basic CSPs which utilize these intercalative effects to enhance enantioselectivity is discussed. These CSPs, designed from mechanistic considerations, are useful in the separation of the enantiomers of a number of chiral amines, amino acid esters and amides, amino alcohols and alcohols. Solution-state NMR evidence, including intermolecular nuclear Overhauser enhancements, and X-ray crystallographic data provide support for the primary chiral recognition mechanism.
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