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Issue 14, 2017
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π–hole interactions at work: crystal engineering with nitro-derivatives

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Abstract

In this manuscript, we report the design, synthesis and X-ray characterization of nitrodiene derivatives that present crucial π–hole interactions involving the nitro group as a π–hole donor. The solid state structures of 1,4-dinitro-1,3-butadiene (1), its co-crystal 1·Diox, and homologous 1,4-dinitro-1,3-pentadiene (2) and 2,4-dinitro-2,4-hexadiene (3) feature competition of lone pair–π–hole interactions with common weak CH⋯O bonding and gradually increased role of the NO2⋯NO2 interactions. Regular evolution of the supramolecular patterns (1 to 3) results in generation of an unprecedented 3D non-covalent framework in 3 that is controlled exclusively by short π–hole contacts (O⋯N = 2.9615(18), 3.1304(18) Å). These findings complement the results of high level ab initio calculations (MP2/def2-TZVP) and unite theory and experiment, thus supporting the functional relevance of this novel π–hole interaction.

Graphical abstract: π–hole interactions at work: crystal engineering with nitro-derivatives

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Publication details

The article was received on 08 Feb 2017, accepted on 13 Mar 2017 and first published on 13 Mar 2017


Article type: Paper
DOI: 10.1039/C7CE00267J
Citation: CrystEngComm, 2017,19, 1933-1937
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    π–hole interactions at work: crystal engineering with nitro-derivatives

    A. Bauzá, A. V. Sharko, G. A. Senchyk, E. B. Rusanov, A. Frontera and K. V. Domasevitch, CrystEngComm, 2017, 19, 1933
    DOI: 10.1039/C7CE00267J

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