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.
LanguageEnglish
Pages161-165
Number of pages4
JournalNew Journal of Chemistry
Volume28
DOIs
Publication statusPublished - 22 Oct 2003

Fingerprint

Trinitrotoluene
Crystal structure
Single crystals
Synchrotrons
X ray powder diffraction
Molecular structure
Hydrogen
Hydrogen bonds
X ray diffraction
2-amino-4,6-dinitrotoluene
4-amino-2,6-dinitrotoluene

Keywords

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

Cite this

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title = "The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene",
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.",
keywords = "2, 4, 6-trinitrotoluene, X-ray powder diffraction, dinitrotoluene, single-crystal analysis, TNT, hydrogen-bonded sheets, hydroxyamine.",
author = "D. Graham and A.R. Kennedy and C.J. McHugh and W.E. Smith and W.I.F. David and K. Shankland and N. Shankland",
year = "2003",
month = "10",
day = "22",
doi = "10.1039/b309792g",
language = "English",
volume = "28",
pages = "161--165",
journal = "New Journal of Chemistry",
issn = "1144-0546",

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The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene. / Graham, D.; Kennedy, A.R.; McHugh, C.J.; Smith, W.E.; David, W.I.F.; Shankland, K.; Shankland, N.

In: New Journal of Chemistry, Vol. 28, 22.10.2003, p. 161-165.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene

AU - Graham, D.

AU - Kennedy, A.R.

AU - McHugh, C.J.

AU - Smith, W.E.

AU - David, W.I.F.

AU - Shankland, K.

AU - Shankland, N.

PY - 2003/10/22

Y1 - 2003/10/22

N2 - 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.

AB - 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.

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KW - hydroxyamine.

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