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

D. Graham, A.R. Kennedy, C.J. McHugh, W.E. Smith, W.I.F. David, K. Shankland, N. Shankland

Research output: Contribution to journalArticle

15 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)161-165
Number of pages4
JournalNew Journal of Chemistry
Volume28
DOIs
Publication statusPublished - 22 Oct 2003

Keywords

  • 2
  • 4
  • 6-trinitrotoluene
  • X-ray powder diffraction
  • dinitrotoluene
  • single-crystal analysis
  • TNT
  • hydrogen-bonded sheets
  • hydroxyamine.

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