NMR as a tool for simultaneous study of diasteroisomeric inclusion complexes, part 2: complexes formed by racemic mixture of 4-hydroxyflavanone and two cyclodextrins

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• 作者：C. Acu?a-Rougier (1)
  C. Jullian (1) cjullian@uchile.cl
  C. Olea-Azar (1) colea@uchile.cl
• 关键词：Cyclodextrin – NMR – Enantiomeric differentiation – ROESY
• 刊名：Journal of Inclusion Phenomena and Macrocyclic Chemistry
• 出版年：2012
• 出版时间：December 2012
• 年：2012
• 卷：74
• 期：1-4
• 页码：157-166
• 全文大小：513.0 KB
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• 作者单位：1. Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Sergio Livingstone 1007, Independencia, Santiago, RM, Chile
• ISSN：1573-1111

文摘

Complexes formed by (±)-4′-hydroxyflavanone (OHFL) and the cyclodextrins β-cyclodextrin and (2-hydroxypropyl)-β-CD were obtained using the racemic mixture of the OHFL. These complexes were able to be studied due to their enantiodifferentiation by 1H-NMR spectroscopy. Stoichiometry, association constants and thermodynamic parameters were obtained from these NMR data, and inclusion geometries were proposed from ROESY spectra. The results show a 1:1 stoichiometry, K _a values decrease with increasing temperature, a spontaneous and exothermic complexes formation, and that ROESY spectra cannot differentiate between enantiomers, and therefore the estimated inclusion geometries were proposed for the mixture of diasteroisomeric complexes.