University of Illinois Urbana-Champaign

A Study of the Interactions Involved in the Direct Liquid Chromatographic Resolution of Racemates

Schreiner, James Louis

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https://hdl.handle.net/2142/70171

Description

Title
A Study of the Interactions Involved in the Direct Liquid Chromatographic Resolution of Racemates
Author(s)
Schreiner, James Louis
Issue Date
1981
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
Abstract
  • The direct resolution of racemates upon a chiral stationary phase (CSP) is becoming a widely used technique. In order to prepare more effective and more specific CSPs, the rationale for resolution should be better understood. Two chiral recognition models of considerable scope are proposed for the resolution of 1,1'-bi-2-naphthol (BBN) and 5-arylhydantoins as their analogs upon a CSP prepared from N-3,5-dinitrobenzoylphenylglycine. The models allow assignment of the configuration of each enantiomer based upon elution order. However, care must be excersized when the substrate is modified drastically. In addition, the attempted resolution of (alpha)-hydroxyphosphonates and simple amides is described.
  • Finally, the facile resolution of BBN and analogs upon the phenylglycine CSP is the basis for preparing a CSP containing a BBN analog. Several attempts to prepare a new CSP are described.
Graduation Semester
1981
Type of Resource
text
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http://hdl.handle.net/2142/70171

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