A Rational Approach to the Design of Highly Effective Chiral Stationary Phases

Resolution of enantiomers on a chromatography column containing a chiral stationary phase is emerging as an outstanding technique for the determination of enantiomeric purity, the assignment of absolute configuration and the preparative resolution of enantiomers. The continued growth of this technique depends upon the development of efficient and broadly applicable chiral stationary phases. Toward this end, the reciprocity concept of chiral recognition, first used in this research group, has been applied with considerable success. If a chiral stationary phase derived from (+)-A can distinguish between (+)-B and (-)-B, then a chiral stationary phase derived from (+)-B may distinguish (+)-A from (-)-A. This simple concept in combination with several proposed chiral recognition mechanisms has led to the design of highly effective hydantion and (alpha)-arylalkylamine based chiral stationary phases. These chiral stationary phases, covalently bonded to 5(mu)m Spherisorb silica gel, are very effective in the resolution of 3,5-dinitrobenzoyl derivatives of amino acids, their analogues, amines and alcohols. Additionally, a number of pharmacologically important compounds, such as the (beta)-adrenergic blocking agents, propranolol and metoprolol (3,5-dinitrobenzoyl derivative), central nervous system stimulant amphetamine (3,5-dinitrobenzoyl derivative) and antiinflammatory agent ibuprofen (3,5-dintiroanilide derivative) also resolved quite well on these chiral stationary phases.

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

2014

Author dc:creator

• Hyun, Myung Ho

• Chemistry, Organic

Identifier

(UMI)AAI8502188

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70276