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A DFT investigation of the host–guest interactions between boron-based aromatic systems and β-cyclodextrin

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Abstract

Density functional theory calculations including dispersion at BLYP-D3(BJ)/def2-SVP level of theory were performed for a series of systems based on cyclodextrin complexation with boron-based aromatic compounds. Elaborated investigations were carried out using different quantum chemical parameters such as computed complexation energies, theoretical association constants, and natural bond orbital (NBO) analysis. Several configurations and inclusion modes were considered in this work. The calculated complexation energies were consistent with the experimental classification of these systems on the basis of occurring interactions. Reduced density gradient (RDG) and independent gradient model (IGM) approaches determined the nature and strength of non-covalent interactions which played a central role in the formation of the complexes. Thus, phenylboronic acid (PBA) and benzoxaborole (Bxb) act mainly as hydrogen-bonded complexes with β-cyclodextrin, while mainly Van der Waals (vdW) interactions stabilize both catechol (PhBcat) and pinacol esters of phenylboronic acid (PhBpin) complexes. The ferroceneboronic acid (FcBA) exhibits a mixture of H-bonds and vdW interactions with β-cyclodextrin.

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Authors and Affiliations

  1. Department of Chemistry, College of Science and Arts, Qassim University, Ar Rass, Saudi Arabia

    Seyfeddine Rahali

  2. IPEIEM, Research Unit On Fundamental Sciences and Didactics, Université de Tunis El Manar, 2092, Tunis, Tunisia

    Seyfeddine Rahali

  3. Department of Petrochemical and Process Engineering, Faculty of Technology, University of Skikda, El Hadaik Road, P.O. Box 26, 21000, Skikda, Algeria

    Youghourta Belhocine, Abdelaziz Bouhadiba & Ibtissem Meriem Assaba

  4. Department of Technology, Faculty of Technology, University of Skikda, El Hadaik Road, P.O. Box 26, 21000, Skikda, Algeria

    Hamza Allal

  5. UMR 7086, Université de Paris, ITODYS, CNRS, 15 rue J-A de Baïf, 75013, Paris, France

    Mahamadou Seydou

Authors
  1. Seyfeddine Rahali
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  2. Youghourta Belhocine
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  3. Hamza Allal
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  4. Abdelaziz Bouhadiba
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  5. Ibtissem Meriem Assaba
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  6. Mahamadou Seydou
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Contributions

Seyfeddine Rahali: Conceptualization; Formal analysis; Writing — original draft; Investigation. Youghourta Belhocine: Formal analysis; Software; review and editing; Supervision; Validation. Hamza Allal: Methodology; Software; Visualization. Abdelaziz Bouhadiba: Data curation; Formal analysis. Ibtissem Meriem Assaba: Writing — original draft. Mahamadou Seydou: review and editing. All authors provided critical feedback and helped shape the research, analysis, and manuscript.

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Correspondence to Seyfeddine Rahali.

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Rahali, S., Belhocine, Y., Allal, H. et al. A DFT investigation of the host–guest interactions between boron-based aromatic systems and β-cyclodextrin. Struct Chem 33, 195–206 (2022). https://doi.org/10.1007/s11224-021-01835-6

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  • DOI: https://doi.org/10.1007/s11224-021-01835-6

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