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Characterization of Inclusion Interaction between Acylsulfonamide and β-Cyclodextrin: Experimentally and Molecular Modeling Studies

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Abstract

The inclusion complex of acylsulfonamide (ASL) with β-cyclodextrin (β-CD) was explored experimentally and by molecular modeling studies. The stoichiometric ratio of the complex was found to be 1 : 1 and the stability constant was evaluated using the Benesi–Hildebrand equation. Estimation of the thermodynamic parameters of the inclusion complex in vacuum demonstrates that it is an enthalpy driven process phase and an enthalpy–entropy simultaneous process in aqueous solution, which is consistent with the experimental results. Semi-empirical calculations using PM6 and ONIOM2 methods, in vacuum and in water, were undertaken and done. The energetically more favorable structure obtained with the ONIOM2 method leads to the rise of intermolecular hydrogen bonds between acylsulfonamide and β-cyclodextrin. These interactions were probed using the natural bond orbital (NBO).

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Authors and Affiliations

  1. Département de Chimie, Faculté des Sciences Exactes et Informatique Université Mohamed Seddik Ben Yahia-Jijel Ouled Aissa BP 98, 18000, Jijel, Algérie

    Khalil Sahra

  2. Laboratoire de Chimie Physique, Université 08 Mai 45, BP401, 24000, Guelma, Algérie

    Khalil Sahra & Mekki Kadri

  3. Laboratoire de Chimie Organique Appliquée, Groupe Chimie Bio-Organique, Faculté des Sciences, Université Badji Mokhtar, BP 12, Annaba, Algérie

    Malika Berredjem

  4. Département de Chimie Moléculaire (UMR 5250), Université Joseph Fourier/CNRS, Grenoble, France

    Anne Milet

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  1. Khalil Sahra
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  2. Mekki Kadri
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Correspondence to Khalil Sahra.

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Sahra, K., Kadri, M., Berredjem, M. et al. Characterization of Inclusion Interaction between Acylsulfonamide and β-Cyclodextrin: Experimentally and Molecular Modeling Studies. Russ. J. Phys. Chem. 96, 3149–3160 (2022). https://doi.org/10.1134/S0036024423020097

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  • DOI: https://doi.org/10.1134/S0036024423020097

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