180133-38-4Relevant academic research and scientific papers
Intermolecular 1H-1H Two-Dimensional Nuclear Overhauser Enhamncements in the Characterization of a Rationally Designed Chiral Recognition System
Pirkle, William H.,Murray, Patrick G.,Rausch, David J.,McKenna, Stephen T.
, p. 4769 - 4774 (1996)
Chiral stationary phases (CSPs) for liquid chromatography derived from N-(acyl)proline-3,5-dimethylanilides separate the enantiomers of N-(3,5-dinitrobenzoyl)-α-amino esters and amides with high levels of selectivity.These CSPs have been used to assemble a large body of chromatographic data which indirectly supports tha validity of the mechanistic rationalle originally used in the design of these CSPs.We herein report 1H and 13C chemical shift data obtained when the (S)-enantiomer of chiral solvating agent (CSA) 3, and a soluble analogue of the selector used in CSP (S)-1, acts on each of ther enantiomers of the diemthylamide of N-(3,5-dinitrobenzoyl)leucine, 2.The changes in chemical shift in the mixture of (S)-2 and (S)-3 support the existence of those interactions thought to be essential to chiral recognition in this system.In addition, sugnificant intermolecular NOESY enhancements are observed in this mixture.These NOE data are consistent with the structure expected for the more stable diastereomeric adsorbate formed between (S)-2 and the (S)-proline-derived CSP 1.No intermolecular NOEs are observed for corresponding mixtures of the chiral solvating agent (S)-3 and (R)-2, the enantiomer least retained on (S)-CSP 1.
