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Intermolecular interactions in crystals of benzene and its mono- and dinitro derivatives: study from the energetic viewpoint

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Abstract

Intermolecular interactions and their role in the crystal packing formation have been studied in benzene, mono-nitrobenzene and all isomers of dinitrobenzene crystals. In both polymorphic structures of benzene, stacking interactions are absent and weak C–H⋯π hydrogen bonds play the main role in the crystal packing formation. The insertion of nitro groups into the benzene molecule causes the formation of stronger C–H⋯O intermolecular hydrogen bonds and stacking interactions instead of weaker C–H⋯π interactions. The analysis of pairwise interaction energies revealed that the stacking interactions form the primary structural motif in the crystals of nitro-substituted benzenes with the exception of para-dinitrobenzene. The existence of stacking interactions was shown to need not only the special orientation of π-systems but also the polarization of the molecule. It was shown that C–H⋯O hydrogen bonds play the minor role in the crystals of mono- and dinitrobenzenes where these interactions link the primary basic structural motifs. The C–H⋯O hydrogen bonds were shown to be weaker than non-specific interactions in the absence of stacking in the para-dinitrobenzene crystal.

Graphical abstract: Intermolecular interactions in crystals of benzene and its mono- and dinitro derivatives: study from the energetic viewpoint

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Publication details

The article was received on 12 Dec 2018, accepted on 28 Mar 2019 and first published on 28 Mar 2019


Article type: Paper
DOI: 10.1039/C8CE02099J
Citation: CrystEngComm, 2019, Advance Article

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    Intermolecular interactions in crystals of benzene and its mono- and dinitro derivatives: study from the energetic viewpoint

    I. S. Konovalova, S. V. Shishkina, G. Bani-Khaled, E. N. Muzyka and A. N. Boyko, CrystEngComm, 2019, Advance Article , DOI: 10.1039/C8CE02099J

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