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Host–guest binding selectivity of ethylated pillar[5]arene (EtP5A) towards octane, 1,7-octadiene, and 1,7-octadiyne: a computational investigation

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Abstract

Host–guest binding selectivity of the perethylated pillar[5]arene (EtP5A) macrocycles with aliphatic modified hydrocarbons, i.e., octane, 1,7-octadiene, and 1,7-octadiyne as guests, has been investigated computationally employing molecular docking simulations. Density functional theory (DFT) investigations were also performed on these host–guest complexes using the dispersion-corrected approach BLYP-D3(BJ)/TZP/COSMO calculations as implemented in the ADF program and two dispersion-corrected density functionals, ωB97XD and B97D, along with the 6-311G* basis set, coupled with the PCM solvation model as implemented in the Gaussian software. We performed analysis of the frontier molecular orbitals (FMO) and natural bond orbitals (NBO), energy decomposition analysis (EDA), and noncovalent interaction (NCI-RDG) analysis. The study sheds light on the structures and binding energetics of EtP5A with the above-mentioned guests as well as on the physicochemical nature of the noncovalent interactions involved in these host–guest inclusion complexes. Based on the docking simulations, the EtP5A host revealed slightly better binding ability in the complex with the alkyne guest than with the octane and alkene, as corroborated by the EDA analysis. The results showed that the complexation of EtP5A with the hydrocarbons is mainly governed by the interplay of electrostatic interactions and dispersive noncovalent interactions. These results agree well with NCI-RDG and NBO analysis showing that host–guest binding interactions result predominantly from electrostatic C-H···π and van der Waals interactions, the H-bonding being weak or not observed. The results obtained using different computational methods were found to be in good agreement and complementary.

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Data availability

All data generated or analyzed during this study are included in this published article and its supplementary information files.

Code availability

Commercial license. Amsterdam Molecular Simulation AMS2021: www.scm.com. Gaussian 09, Revision B.01: https://gaussian.com/. Open-source. Avogadro version 1.2.0n. http://avogadro.cc/. Molden version 5.8.2: https://www.theochem.ru.nl/molden/. Multiwfn: http://sobereva.com/multiwfn/. AutoDock and AutoDockTools: http://autodock.scripps.edu; http://mgltools.scripps.edu/downloads. Aleksey Kuznetsov appreciates computational facilities of the Department of Chemistry, ITA, Brazil.

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Acknowledgements

We acknowledge the Algerian PRFU project (2022–2024: Grant No. B00L01EN250120220001) and the French GENCI IDRIS and GENCI-CINES for an allocation of computing time (Grant No. 2021-080649).

Funding

Aleksey Kuznetsov appreciates the financial support of USM and computational facilities of the Department of Chemistry, ITA, Brazil.

Author information

Authors and Affiliations

  1. Laboratoire de Physique Mathématique et Subatomique LPMS, Département de Chimie, Université des Frères Mentouri, 25017, Constantine, Algeria

    Adel Krid & Lotfi Belkhiri

  2. Centre de Recherche en Sciences Pharmaceutiques CRSP, Nouvelle Ville, Zone d’activité ZAM, Constantine, Algeria

    Adel Krid & Lotfi Belkhiri

  3. Département Génie Mécanique, Faculté de Technologie, Université, 20 Aout, 1955, Skikda, Algeria

    Hamza Allal

  4. Department of Chemistry, Universidad Técnica Federico Santa Maria, Av. Santa Maria 6400, 7660251, Vitacura Santiago, Chile

    Aleksey Kuznetsov

  5. ISCR UMR 6226, Univ Rennes, CNRS, Campus de Beaulieu, 35042, Rennes Cedex, France

    Abdou Boucekkine

Authors
  1. Adel Krid
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  2. Lotfi Belkhiri
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  3. Hamza Allal
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  4. Aleksey Kuznetsov
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  5. Abdou Boucekkine
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Contributions

Adel Krid, conceptualization, investigation, material preparation, and data collection. Lotfi Belkhiri, formal analysis, project administration, supervision, and writing — original draft. Hamza Allal, methodology, software, and validation. Aleksey Kuznetsov, conceptualization, writing — original draft, supervision, investigation, data collection, software, and validation. Abdou Boucekkine, writing — review and editing, and supervision.

Corresponding author

Correspondence to Lotfi Belkhiri.

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Krid, A., Belkhiri, L., Allal, H. et al. Host–guest binding selectivity of ethylated pillar[5]arene (EtP5A) towards octane, 1,7-octadiene, and 1,7-octadiyne: a computational investigation. Struct Chem 34, 625–638 (2023). https://doi.org/10.1007/s11224-022-02002-1

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  • DOI: https://doi.org/10.1007/s11224-022-02002-1

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