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

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.

[1]  A. Huq,et al.  Subtleties in crystal structure solution from powder diffraction data using simulated annealing: ranitidine hydrochloride. , 2003, Journal of pharmaceutical sciences.

[2]  K. Thorn,et al.  15N NMR investigation of the covalent binding of reduced TNT amines to soil humic acid, model compounds, and lignocellulose. , 2002, Environmental science & technology.

[3]  K. Shankland,et al.  Molecular, crystallographic and algorithmic factors in structure determination from powder diffraction data by simulated annealing , 2002 .

[4]  Duncan Graham,et al.  SERRS. In situ substrate formation and improved detection using microfluidics. , 2002, Analytical chemistry.

[5]  Z. Urbańczyk-Lipkowska,et al.  Cooperative effect of multiple hydrogen bonding involving the nitro group: solid state dimeric self-assembly of o-, m- and p-hydroxyphenyl-2,4-dinitrophenylhydrazones , 2002 .

[6]  J. Murray,et al.  Phytodetoxification of TNT by transgenic plants expressing a bacterial nitroreductase , 2001, Nature Biotechnology.

[7]  J. Ramos,et al.  Biological Degradation of 2,4,6-Trinitrotoluene , 2001 .

[8]  N. Bunce,et al.  Electrochemical treatment of 2,4,6-trinitrotoluene and related compounds. , 2001, Environmental science & technology.

[9]  Hong-Gyu Song,et al.  Simultaneous Utilization of Two Different Pathways in Degradation of 2,4,6-Trinitrotoluene by White Rot Fungus Irpex lacteus , 2000 .

[10]  K. Shankland,et al.  The disordered structure of tetraferrocenyl-[3]-cumulene, (Fc)2C=C=C=C(Fc)2, by simulated annealing using synchrotron powder diffraction data , 2000 .

[11]  Z. Urbańczyk-Lipkowska,et al.  Competition between π–π stacking and hydrogen bonding in (1:2) picrates of 1,5-diamino-3-oxapentane, 1,8-diamino-3,6-dioxaoctane and 1,5-diamino-3-azapentane—solid state studies , 2000 .

[12]  Robin Taylor,et al.  Intermolecular Nonbonded Contact Distances in Organic Crystal Structures: Comparison with Distances Expected from van der Waals Radii , 1996 .

[13]  J. Klinowski,et al.  Attractive Inter- and Intramolecular N.cntdot..cntdot..cntdot.O Interactions in N,N-Dipicrylamine and Its Ionic Complexes , 1994 .

[14]  A. Stone,et al.  The Nature of -Cl.cntdot..cntdot..cntdot.Cl- Intermolecular Interactions , 1994 .

[15]  A. Domenicano.  Structural Substituent Effects in Benzene Derivatives , 1992 .

[16]  D. Louër,et al.  Indexing of powder diffraction patterns for low-symmetry lattices by the successive dichotomy method , 1991 .

[17]  J. Maurin,et al.  Crystallographic studies and physicochemical properties of π-electron systems: Part XIV. Crystal and molecular structure of N,N-dimethyl-p-nitroanaline , 1988 .

[18]  A. Bondi.  van der Waals Volumes and Radii , 1964 .