University of Illinois Urbana-Champaign

Preparation and evaluation of several new pi-basic chiral stationary phases

Deming, Kris Carl

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Description

Title
Preparation and evaluation of several new pi-basic chiral stationary phases
Author(s)
Deming, Kris Carl
Issue Date
1989
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
Language
eng
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.
Type of Resource
text
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http://hdl.handle.net/2142/21522
Copyright and License Information
Copyright 1989 Deming, Kris Carl

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