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NMR as a tool for simultaneous study of diastereoisomeric inclusion complexes formed by racemic mixture of 4′-hydroxyflavanone and heptakis-(2,6-O-dimethyl)-β-cyclodextrin

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Abstract

The complexes formed by (±)-4′-hydroxyflavanone (OHFL) and heptakis-(2,6-O-dimethyl)-β-cyclodextrin (DM-β-CD) were obtained using the racemic mixture of 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 and docking experiments. The results show that diastereoisomeric complexes can be studied even when they are formed by enantiomeric mixtures.

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Acknowledgments

C. A. R thanks to CONICYT PhD scholarship, DPP scholarship stay, Fondecyt project 11080038 and CONICYT project 24091026; R. M. A. thanks to CONICYT PhD scholarship, and to S. Miranda.

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Authors and Affiliations

  1. Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Sergio Livingstone 1007, Independencia, Santiago, RM, Chile

    C. Acuña-Rougier, R. Mera-Adasme, C. Jullian & C. Olea-Azar

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  1. C. Acuña-Rougier
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  2. R. Mera-Adasme
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  3. C. Jullian
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  4. C. Olea-Azar
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Correspondence to C. Jullian or C. Olea-Azar.

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Acuña-Rougier, C., Mera-Adasme, R., Jullian, C. et al. NMR as a tool for simultaneous study of diastereoisomeric inclusion complexes formed by racemic mixture of 4′-hydroxyflavanone and heptakis-(2,6-O-dimethyl)-β-cyclodextrin. J Incl Phenom Macrocycl Chem 68, 339–346 (2010). https://doi.org/10.1007/s10847-010-9793-5

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