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The association of π–π stacking and hydrogen bonding interactions in substituted Rebek imide with 2,6-di(isobutyramido)pyridine rings: theoretical insight into X-Rebek imide||pyr complexes

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Abstract

A host–guest model designed between two hemispheres as Rebek imide receptor and different ligands via triple hydrogen bonding and π−π stacking interactions was surveyed to investigate the substituent effects. The association of Rebek imide with 2,6-di(isobutyramido)pyridine (X-Rebek imide||pyr) in the presence of electron donating/withdrawing substituents was studied (X = (NCH3)2, OCH3, CH3, OH, H, F, Cl, Br and CN, CF3 and NO2, where || and ∙∙∙ denote π–π stacking and hydrogen bonding). It was explained the variation in binding energies, energy decomposition, geometries, NMR properties, and electron density of mentioned complexes and effect of different types of the substituents in studied complexes was identified via computational chemistry at M05-2X/6-311++G** level of theory on π–π stacking and hydrogen bonding interactions.

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Authors and Affiliations

  1. Department of Chemistry, Payame Noor University, P.O. Box: 19395-3697, Tehran, Iran

    Sabereh Parvizi Moghadam & Reza Behjatmanesh-Ardakani

  2. Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, P.O. Box 77139-36417, Rafsanjan, Iran

    Marziyeh Mohammadi

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  1. Sabereh Parvizi Moghadam
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  2. Marziyeh Mohammadi
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Parvizi Moghadam, S., Mohammadi, M. & Behjatmanesh-Ardakani, R. The association of π–π stacking and hydrogen bonding interactions in substituted Rebek imide with 2,6-di(isobutyramido)pyridine rings: theoretical insight into X-Rebek imide||pyr complexes. Struct Chem 31, 747–754 (2020). https://doi.org/10.1007/s11224-019-01450-6

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  • DOI: https://doi.org/10.1007/s11224-019-01450-6

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