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

Several new chiral stationary phases (CSPs) derived from α-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 α- and β-amino esters and amides, amines, amino alcohols, alcohols and α-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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Deming, Kris Carl

Contributors dc:contributor

• Pirkle, William H.

• Chemistry, Analytical
• Chemistry, Organic

Statement dc:rights

• Copyright 1989 Deming, Kris Carl

Language dc:language

eng

Identifier

AAI9010844
(UMI)AAI9010844

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/21522