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

Duncan Graham, Alan R. Kennedy, Callum J. McHugh, W.Ewen Smith, William I.F. David, Kenneth Shankland, Norman Shankland

Research output: Contribution to journalArticle

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 pages5
JournalNew Journal of Chemistry
Volume28
DOIs
Publication statusPublished - 2004
Externally publishedYes

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

Cite this

Graham, Duncan ; Kennedy, Alan R. ; McHugh, Callum J. ; Smith, W.Ewen ; David, William I.F. ; Shankland, Kenneth ; Shankland, Norman. / The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene. In: New Journal of Chemistry. 2004 ; Vol. 28. pp. 161-165.
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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.",
author = "Duncan Graham and Kennedy, {Alan R.} and McHugh, {Callum J.} and W.Ewen Smith and David, {William I.F.} and Kenneth Shankland and Norman Shankland",
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language = "English",
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The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene. / Graham, Duncan; Kennedy, Alan R.; McHugh, Callum J.; Smith, W.Ewen; David, William I.F.; Shankland, Kenneth; Shankland, Norman.

In: New Journal of Chemistry, Vol. 28, 2004, 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, Duncan

AU - Kennedy, Alan R.

AU - McHugh, Callum J.

AU - Smith, W.Ewen

AU - David, William I.F.

AU - Shankland, Kenneth

AU - Shankland, Norman

PY - 2004

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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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JO - New Journal of Chemistry

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