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Issue 15, 2011
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The C–Cl⋯π interactions inside supramolecular nanotubes of hexaethynylhexamethoxy[6]pericyclyne

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Abstract

Model complexes of hexaethynylhexamethoxy[6]pericyclyne (HM6P) molecules, with or without dichloromethane (DCM) guests, have been calculated at the M05-2X/6-311G(d,p) DFT level. Analysis of nonbonding interactions shows that the cohesion of the supramolecular tubular assemblies previously observed in the crystal state, relies mainly on C–H⋯O hydrogen bonds between axial ethynyl and equatorial methoxy substituents of stacked HM6P C18 macrocycles in a cyclohexane-like chair conformation. The intrinsic binding energy of one HM6P molecule with two neighbors is calculated to be more than 40 kcal mol−1. The inner channel of the stacks (of ca. 8 Å diameter) are suitable for hosting DCM molecules. Using the Atoms In Molecules (AIM) theory, the interaction between DCM molecules and surrounding triple bonds is analyzed in terms of σ-hole-directed C–Cl⋯π halogen bonds. A σ-hole-directed Cl⋯Cl interaction between two chlorine atoms of different DCM molecules is also evidenced.

Graphical abstract: The C–Cl⋯π interactions inside supramolecular nanotubes of hexaethynylhexamethoxy[6]pericyclyne

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Publication details

The article was received on 25 Nov 2010, accepted on 11 Feb 2011 and first published on 14 Mar 2011


Article type: Paper
DOI: 10.1039/C0CP02666B
Citation: Phys. Chem. Chem. Phys., 2011,13, 6837-6848
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    The C–Cl⋯π interactions inside supramolecular nanotubes of hexaethynylhexamethoxy[6]pericyclyne

    O. V. Shishkin, R. I. Zubatyuk, V. V. Dyakonenko, C. Lepetit and R. Chauvin, Phys. Chem. Chem. Phys., 2011, 13, 6837
    DOI: 10.1039/C0CP02666B

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