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

  • Ines Béjaoui
  • Mondher Baâzaoui
  • Yves Chevalier
  • Noureddine Amdouni
  • Rafik Kalfat
  • Souhaira Hbaieb
Original Article


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: AdCOONa+) 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.


Pyridinium-β-cyclodextrins Adamantane derivatives Inclusion complexes 1H NMR Apparent binding constant 



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

Supplementary material

10847_2016_643_MOESM1_ESM.docx (2.4 mb)
Supplementary material 1 (DOCX 2428 kb)


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Copyright information

© Springer Science+Business Media Dordrecht 2016

Authors and Affiliations

  • Ines Béjaoui
    • 1
    • 4
  • Mondher Baâzaoui
    • 1
    • 4
  • Yves Chevalier
    • 2
  • Noureddine Amdouni
    • 1
  • Rafik Kalfat
    • 3
  • Souhaira Hbaieb
    • 3
    • 5
  1. 1.UR Physico-Chimie des Matériaux SolidesFaculté des Sciences de TunisTunisTunisia
  2. 2.Laboratoire d’Automatique et de Génie des ProcédésUMR 5007 CNRS, Université de Lyon 1Villeurbanne CedexFrance
  3. 3.Laboratoire Matériaux, Traitement et AnalyseINRAP, Biotechpole Sidi-ThabetArianaTunisie
  4. 4.Faculté des sciences de BizerteBizerteTunisia
  5. 5.Faculté des Sciences de Tunis, Université Tunis El ManarTunisTunisie

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