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Quantitative analysis of intermolecular forces for hydrogen bond driven self-assembly of resorcinol and bis(pyridine) substituted ethylene cocrystals, before and after [2 + 2] dimerization

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Abstract

The long-range and dispersion corrected density functional theory (DFT + Disp), and Møller–Plesset second-order perturbation theory (MP2) were used for describing the intermolecular interactions between hydrogen bond driven self-assembly of 2(5-CN-res) … 2(4,4′-bpe) and 2(4,6-diCl-res) … 2(4,4′-bpe) cocrystals [where 5-CN-res = 5-cyanoresorcinol, 4,6-diCl-res = 4,6-dichlororesorcinol, and 4,4′-bpe = trans-1,2-bis(4-pyridyl)ethylene], before and after [2 + 2] dimerization to 2(5-CN-res) … (4,4′-tpcb) and 2(4,6-diCl-res) … (4,4′-tpcb), respectively [where 4,4′-tpcb = 1,2,3,4-tetra(4-pyridyl)cyclobutane]. The nature and strength of intermolecular forces were studied using the absolutely localized molecular orbitals energy decomposition analysis, and the plot of reduced density gradient versus the electron density multiplied by the sign of the second Hessian eigenvalue [sign(λ2)ρ]. The results show that the interaction of 2(4,4′-bpe) is basically dispersive nature, while all of the electrostatic, dispersion, polarization and charge-transfer interactions are largely contributed to the interaction energy of 2(4,4′-bpe) with 5-CN-res and 4,6-diCl-res molecules. The total interaction energy of complexes before dimerization is greater than that after dimerization. Since the contribution of polarization and charge-transfer interactions after dimerization are nearly unchanged, the main difference in the interaction energy of complexes is due to the weaker contribution of van der Waals and electrostatic forces in the products.

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Acknowledgments

We would like to thank the Isfahan University of Technology’s research council for its financial support.

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  1. Department of Chemistry, Isfahan University of Technology, 84156-83111, Isfahan, Iran

    Mehdi Zamani & Hossein A. Dabbagh

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  1. Mehdi Zamani
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Correspondence to Hossein A. Dabbagh.

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Zamani, M., Dabbagh, H.A. Quantitative analysis of intermolecular forces for hydrogen bond driven self-assembly of resorcinol and bis(pyridine) substituted ethylene cocrystals, before and after [2 + 2] dimerization. Struct Chem 24, 1597–1605 (2013). https://doi.org/10.1007/s11224-012-0197-6

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  • DOI: https://doi.org/10.1007/s11224-012-0197-6

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