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Structural elucidation of supramolecular alpha-cyclodextrin dimer/aliphatic monofunctional molecules complexes

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Abstract

The structural elucidation of 2α-cyclodextrin/1-octanethiol, 2α-cyclodextrin/1-octylamine and 2α-cyclodextrin/1-nonanoic acid inclusion complexes by nuclear magnetic resonance (NMR) spectroscopy and molecular modeling has been achieved. The detailed spatial configurations are proposed for the three inclusion complexes based on 2D NMR method. ROESY experiments confirm the inclusion of guest molecules inside the α-cyclodextrin (α-CD) cavity. On the other hand, the host-guest ratio observed was 2:1 for three complexes. The detailed spatial configuration proposed based on 2D NMR methods were further interpreted using molecular modeling studies. The theoretical calculations are in good agreement with the experimental data.

Supramolecular alpha-cyclodextrin dimer/aliphatic monofunctional molecules complexes

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Acknowledgments

This research was possible thanks to financial support of Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT), grants Nos. 11110138, 1090029, 1080505. L.B.P wants to thanks Basal Financing Program CONICYT, FB0807 (CEDENNA).

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Authors and Affiliations

  1. Departamento de Química, Facultad de Ciencias Básicas, Universidad Metropolitana de Ciencias de la Educación, Santiago, Chile

    L. Barrientos & C. Orellana

  2. Center for the Development of Nanoscience and Nanotechnology, CEDENNA, Santiago, Chile

    L. Barrientos & C. Orellana

  3. CEM, Departamento de Biología, Facultad de Ciencias, Universidad de Chile, Santiago, Chile

    E. Lang

  4. Departamento de Química Inorgánica y Analítica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile

    G. Zapata-Torres & C. Celis-Barros

  5. Departamento de Química, Facultad de Ciencias, Universidad de Chile, Santiago, Chile

    P. Jara & N. Yutronic

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  1. L. Barrientos
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  2. E. Lang
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  3. G. Zapata-Torres
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  4. C. Celis-Barros
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  5. C. Orellana
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  6. P. Jara
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  7. N. Yutronic
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Correspondence to L. Barrientos.

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Barrientos, L., Lang, E., Zapata-Torres, G. et al. Structural elucidation of supramolecular alpha-cyclodextrin dimer/aliphatic monofunctional molecules complexes. J Mol Model 19, 2119–2126 (2013). https://doi.org/10.1007/s00894-012-1675-x

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  • DOI: https://doi.org/10.1007/s00894-012-1675-x

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