Abstract
In aqueous solution, the apparent association constant at room temperature for the 1 : 1 inclusion of S-(+)-carvone in β- cyclodextrin is double of that for R-(-)-carvone, whereas, at 45 °C, both enantiomers have association constants two orders of magnitude smaller, with the S-(+) inclusion being then slightly weaker than the R-(-) encapsulation. Calculations carried out at the molecular mechanics, AM1 and STO-3G levels confirm the preferential inclusion of the S-enantiomer and provide important clues for understanding chiral discrimination by β-cyclodextrin.
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Da Silva, A.M., Empis, J. & Teixeira-Dias, J.J. Inclusion of Enantiomeric Carvones in β-Cyclodextrin: a Variable Temperature 1H NMR Study in Aqueous Solution. Journal of Inclusion Phenomena 33, 81–97 (1999). https://doi.org/10.1023/A:1008013810427
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DOI: https://doi.org/10.1023/A:1008013810427