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The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene

Graham, D. and Kennedy, A.R. and McHugh, C.J. and Smith, W.E. and David, W.I.F. and Shankland, K. and Shankland, N. (2003) The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene. New Journal of Chemistry, 28. pp. 161-165. ISSN 1144-0546

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Abstract

The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene (TNT) have been determined by synchrotron X-ray powder diffraction (2-amino-4,6-dinitrotoluene) and single crystal X-ray diffraction (4-amino-2,6-dinitrotoluene and 2-hydroxyamino-4,6-dinitrotoluene). The molecular structure of 2-amino-4,6-dinitrotoluene, including rotational disorder of the 6-nitro group, was subsequently detailed to a higher resolution by a single-crystal analysis. In contrast to the known structures of TNT, the crystal structures of these amino species are dominated by hydrogen-bonded sheets connected via ring stacking, whilst that of 2-hydroxyamino-4,6-dinitrotoluene is dominated by the dual hydrogen-bonding acceptor/donator role of the hydroxyamine group.