Application of L-proline derivatives as chiral shift reagents for enantiomeric recognition of carboxylic acids |
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Authors: | Naziroglu Hayriye Nevin Durmaz Mustafa Bozkurt Selahattin Sirit Abdulkadir |
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Institution: | Department of Chemistry, Karamanoglu Mehmetbey University, Karaman, Turkey. |
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Abstract: | Four proline-derived chiral receptors 5-8 were readily synthesized starting from L-proline. The enantiomeric recognition ability of chiral receptors was examined with a series of carboxylic acids by (1) H NMR spectroscopy. The molar ratio and the association constants of the chiral compounds with each of the enantiomers of guest molecules were determined by using Job plots and a nonlinear least-squares fitting method, respectively. The Job plots indicate that the hosts form 1:1 instantaneous complexes with all guests. The receptors exhibited different chiral recognition abilities toward the enantiomers of racemic guests. Among the chiral receptors used in this study, prolinamide 6 was found to be the best chiral shift reagent and is effective for the determination of the enantiomeric excess of chiral carboxylic acids. |
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Keywords: | chiral recognition L‐proline carboxylic acid NMR titration enantiomeric excess |
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