2,3,4,5,6‐Pentanitroaniline 1,2‐dichloroethane disolvate: `push–pull' deformation of aromatic rings by intramolecular charge transfer |
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Authors: | Sergiy V Rosokha Jian Jiang Lu Sergey M Dibrov Jay K Kochi |
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Abstract: | The title compound, C6H2N6O10·2C2H4Cl2, forms layered stacks of pentanitroaniline molecules, which possess twofold symmetry. The voids between these stacks are occupied by dichloroethane molecules, which reside near a 2/m symmetry element and display pseudo‐inversion symmetry. The C atoms in one of the two solvent molecules are threefold disordered. In the pentanitroaniline molecule, considerable distortion of the benzenoid ring, coupled with the short C—N(H2) bond and out‐of‐plane NO2 twistings, point to significant intramolecular `push–pull' charge transfer at the amino‐ and nitro‐substituted (ortho and para) positions, as theoretically quantified by natural bond orbital analysis of the π‐electron density. |
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