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Influence of the substitution of β-cyclodextrins by pyridinium groups on the complexation of adamantane derivatives

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Abstract

A series of positively charged β-cyclodextrin derivatives have been synthesized by selective functionalization of β-cyclodextrin at the primary rim with pyridinium groups. Characterisation of the modified β-cyclodextrin was done by elementary analysis, FTIR, 1H and 13C NMR spectroscopy. The inclusion complexation of adamantane derivatives (Adamantan-1-ol: AdOH and Sodium adamantane-1-carboxylate: AdCOO−Na+) by the host β-cyclodextrin and its grafted pyridinium derivatives has been investigated using 1H NMR spectroscopy. The stoichiometry of the complexes was found to be in 1:1 (adamantane:β-cyclodextrin) ratio. 1H chemical shift changes of adamantane protons were used to calculate the apparent binding constants of the complexes. Two dimentional NOESY experiments were performed to allow the mode of binding. Mono- and per-charged β-cyclodextrin showed an enhancement of inclusion binding ability towards the sodium adamantane-1-carboxylate guest. The origin of the observed enhancement in the stability of the complexes was ascribed to electrostatic interaction between carboxylate ion and charged pyridinium groups. A simple thermodynamic model of the electrostatic contribution to the complexation is presented.

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Acknowledgments

This work was supported by a Grant from French–Tunisian cooperation project (CMCU n°04S1207).

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Authors and Affiliations

  1. UR Physico-Chimie des Matériaux Solides, Faculté des Sciences de Tunis, Manar II, 2092, Tunis, Tunisia

    Ines Béjaoui, Mondher Baâzaoui & Noureddine Amdouni

  2. Laboratoire d’Automatique et de Génie des Procédés, UMR 5007 CNRS, Université de Lyon 1, 69622, Villeurbanne Cedex, France

    Yves Chevalier

  3. Laboratoire Matériaux, Traitement et Analyse, INRAP, Biotechpole Sidi-Thabet, 2020, Ariana, Tunisie

    Rafik Kalfat & Souhaira Hbaieb

  4. Faculté des sciences de Bizerte, Zarzouna, 7021, Bizerte, Tunisia

    Ines Béjaoui & Mondher Baâzaoui

  5. Faculté des Sciences de Tunis, Université Tunis El Manar, Campus universitaire ElManar, Tunis, Tunisie

    Souhaira Hbaieb

Authors
  1. Ines Béjaoui
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  2. Mondher Baâzaoui
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  3. Yves Chevalier
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  4. Noureddine Amdouni
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  5. Rafik Kalfat
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  6. Souhaira Hbaieb
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Correspondence to Souhaira Hbaieb.

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Béjaoui, I., Baâzaoui, M., Chevalier, Y. et al. Influence of the substitution of β-cyclodextrins by pyridinium groups on the complexation of adamantane derivatives. J Incl Phenom Macrocycl Chem 86, 79–92 (2016). https://doi.org/10.1007/s10847-016-0643-y

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  • DOI: https://doi.org/10.1007/s10847-016-0643-y

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