A Rational Approach to the Design of Highly Effective Chiral Stationary Phases
Hyun, Myung Ho
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https://hdl.handle.net/2142/70276
Description
Title
A Rational Approach to the Design of Highly Effective Chiral Stationary Phases
Author(s)
Hyun, Myung Ho
Issue Date
1984
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
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.
To explain the chromatographic resolution results, chiral recognition models involving three simultaneous stereochemically dependent interactions and the possibility of multiple and competing chiral recognition processes are suggested.
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