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Quantum chemical investigations on hydrogen bonding interactions established in the inclusion complex β-cyclodextrin/benzocaine through the DFT, AIM and NBO approaches

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Abstract

Structure and stability of an inclusion complex formed by Benzocaine (BZC) and β-cyclodextrin (β-CD) were investigated computationally using different levels of theory. The conformational research based on PM6 method allowed reach two minimum-energy structures: model A and model B. The lowest conformers have been exposed to fully geometry optimization employing four DFT functionals: B3LYP, CAM-B3LYP, M05-2X and M06-2X. The performed DFT calculations have identified the model B, in which the amino group is located at the primary face of β-CD, as the most stable complex by an amount up to −40 kcal/mol. Further, the greater stabilization of model B in respect to model A, has been ascertained through AIM and NBO analyses which clarified the main hydrogen bonds HBs interactions governing the reactivity of BZC inside the hydrophobic cavity of β-CD. Finally, the estimated isotropic 1H nuclear magnetic shielding constants generated from the gauge-including-atomic-orbital calculation have been analyzed and then compared with the available experimental data.

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Acknowledgements

The authors would like to thank the General Direction of Scientific Research and Technological Development (DGRSDT) and the National Research Fund (FNR) for funding this work, through project PNR (8/u23/830).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Badji-Mokhtar University, BP 12, Annaba, Algeria

    Hassina Attoui Yahia, Roubila Belghiche & Amel Bouzitouna

  2. Applied Organic Chemistry Laboratory, Department of Chemistry, Faculty of Science, Badji-Mokhtar University, BP 12, Annaba, Algeria

    Ouassila Attoui Yahia

  3. Computational Chemistry and Nanostructures Laboratory, University 8 May 45 of Guelma, Guelma, Algeria

    Djameleddine Khatmi

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  1. Hassina Attoui Yahia
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Attoui Yahia, H., Attoui Yahia, O., Khatmi, D. et al. Quantum chemical investigations on hydrogen bonding interactions established in the inclusion complex β-cyclodextrin/benzocaine through the DFT, AIM and NBO approaches. J Incl Phenom Macrocycl Chem 89, 353–365 (2017). https://doi.org/10.1007/s10847-017-0753-1

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