Title: A rational approach to the design of highly-effective chiral stationary phases
Abstract: Geometric considerations require that a minimum of three simultaneous interactions occur if a chiral molecule is to "recognize" the chirality of other molecules. Moreover, chiral recognition is reciprocal in that if a chiral stationary phase (CSP) derived from (+)-A can distinguish between (+)-B and (−)-B, then a CSP derived from (+)-B may distinguish (+)-A from (−)-A. These simple considerations have been instrumentally applied in the design of a series of CSPs which show great scope and power in the separation of stereoisomers and it is evident that these CSPs have the ability to separate the enantiomers of thousands of amines, amino alcohols, amino acids (and their ester and amide derivatives), alcohols, and diols, all as the 3,5-dinitrobenzoyl derivatives. Specific resolutions are presented for each of the aforementioned classes of compounds, and the relationship of analyte structure to the extent of enantiomer separation is considered. Such relationships are important to the determination of chiral recognition mechanisms. Evidence is presented for the presence of multiple competing chiral recognition mechanisms, and it is demonstrated that this mechanistic understanding can be used to design CSPs in which the balance between the competing mechanisms can be dramatically shifted.
Publication Year: 1984
Publication Date: 1984-01-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 184
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