An X-Ray Study of Symmetrical Trinitrotoluene and Cyclo Trimethylenetrinitramine

Hultgren, Ralph

doi:10.1063/1.1749756

Cited by 23 publications

(17 citation statements)

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“…In 1936, Hultgren reported values for room-temperature lattice parameters for the orthorhombic phase leading to a density of 1.726 g cm -3 with Z = 16 molecules per unit-cell (see Table 1) [5]. This may have been reproduced by Winchell, as in his compilation, it is written that TNT is orthorhombic with a melting temperature of 81°C [6].…”

Section: Crystallographic Datamentioning

confidence: 99%

Topological pressure-temperature state diagram of the crystalline dimorphism of 2,4,6-trinitrotoluene

Céolin

Rietveld

2020

Fluid Phase Equilibria

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The phase behavior of explosive substances is important for the proper design of stable explosive devices. However, the equilibrium behavior of chemical compounds can be difficult to assess, because thermodynamic and kinetic behaviors are generally convoluted in the experimental results. The phase behavior of TNT is a case in point. A thorough review of the literature data demonstrates that the orthorhombic polymorph is the most stable under ambient conditions. Using the topological approach for the construction of a pressure-temperature phase diagram, it can be shown that all data is consistent with an overall enantiotropic system. Nonetheless, it is also clear that the differences between the orthorhombic and the monoclinic polymorphs are relatively small and that the driving force of interconversion between the two under ambient conditions is therefore limited.

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Section: Crystallographic Datamentioning

confidence: 99%

Topological pressure-temperature state diagram of the crystalline dimorphism of 2,4,6-trinitrotoluene

Céolin

Rietveld

2020

Fluid Phase Equilibria

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“…For related literature, see: Akhavan (2004); Bachmann & Sheehan (1949); Brockman et al (1949); Choi & Prince (1972); Ciezak et al (2007); Davidson et al (2008); Harris et al (1959); Henning (1899); von Herz et al (1920); Hultgren (1936); McCrone (1950); Yi & Cai (2008).…”

Section: Related Literaturementioning

confidence: 99%

“…It is of interest with respect to energetic compounds. The structure was originally investigated through X-ray diffraction by Hultgren [(1936). J. Chem.…”

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confidence: 99%

Redetermination ofcyclo-trimethylenetrinitramine

Hakey

Ouellette

Zubieta

et al. 2008

Acta Crystallogr E Struct Rep Online

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The redetermined structure of 1,3,5-trinitro-1,3,5-triazacyclohexane, C3H6N6O6, at 90 (2) K has orthorhombic (Pbca) symmetry. It is of interest with respect to energetic compounds. The structure was originally investigated through X-ray diffraction by Hultgren [(1936). J. Chem. Phys. 4, 84]. Later X-ray investigations were completed by McCrone [(1950). Anal. Chem. 22, 954–955] and Harris, Reed & Gluyas [(1959). AFOSR-TR-59-165 Ohio State University Research Foundation, Columbus, Ohio, USA]. A single-crystal neutron diffraction study was performed by Choi & Prince [(1972). Acta Cryst. B28, 2857–2862] to ascertain the H-atom positions, which had not been defined by the earlier X-ray diffraction studies. All previous studies were performed at or near room temperature. The structure provided is the α polymorph of the title compound. The ring atoms are arranged in the chair conformation with two nitro groups occupying pseudo-equatorial positions and the remaining nitro group is axial. The crystal packing is stabilized by close intramolecular interactions from one H atom in each methylene group to O atoms of adjacent nitro groups, ranging from 2.251 to 2.593 Å.

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“…Modern explosives derive most of their energy either a) from oxidation of the carbon backbone (traditional energetic materials), [3] or b) from their high positive heats of formation. Examples for the first class are explosives such as TNT (1,3,5-trinitrotoluene), [4] RDX (cyclo-1,3,5-trimethylene-2,4,6-trinitramine), [5] and HMX (cyclo-1,3,5,7-tetramethylene-2,4,6,8-tetranitramine). [6] Modern nitro compounds such as CL-20, [7] TEX, [8] or the hepta-and octanitrocubanes [9] possess very high densities and have enhanced energetic properties owing to their substantial cage strain.…”

Section: Introductionmentioning

confidence: 99%

“…the heats of formation, range from values assigned to the group of propellants(4) to values of high explosives(5,7,8). Unfortunately, most of the compounds show low decomposition temperatures in the range 120-150 8C.…”

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confidence: 99%

New Energetic Materials: Functionalized 1‐Ethyl‐5‐aminotetrazoles and 1‐Ethyl‐5‐nitriminotetrazoles

Stierstorfer

Tarantik

Klapötke

2009

Chemistry A European J

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Alkylation of 5-aminotetrazole (1) with 2-chloroethanol leads to a mixture of the N-1 and N-2 isomers of (2-hydroxyethyl)-5-aminotetrazole. Treatment of 1-(2-hydroxyethyl)-5-aminotetrazole (2) with SOCl(2) yielded 1-(2-chlorethyl)-5-aminotetrazole (3). 1-(2-Azidoethyl)-5-aminotetrazole (4) was generated by the reaction of 3 with sodium azide. Nitration of 2, 3, and 4 with HNO(3) (100%) yielded in the case of 2 and 3 1-(2-hydroxyethyl)-5-nitriminotetrazole (5) and 1-(2-chloroethyl)-5-nitriminotetrazole (6). In the case of 4, 1-(2-nitratoethyl)-5-nitriminotetrazole monohydrate (7) was obtained. 1-(2-Azidoethyl)-5-nitriminotetrazole (8) could be obtained by nitration of 4 with NO(2)BF(4) via the formation of potassium 1-(2-azidoethyl)-5-nitriminotetrazolate (9). The reaction of 6 with NaN(3) resulted in the formation of the salt sodium 1-(2-chloroethyl)-5-nitriminotetrazolate (10 a). The deprotonation reaction of 6 was further investigated by the formation of the ammonium salt (10 b). The protonation of 2 and 4 with dilute nitric acid led to 1-(2-hydroxyethyl)-5-aminotetrazolium nitrate (11) and 1-(2-azidoethyl)-5-aminotetrazolium nitrate (12), respectively. Similarly, protonation of 4 with perchloric acid led to 1-(2-azidoethyl)-5-aminotetrazolium perchlorate monohydrate (13). Since 5-nitrimino-tetrazoles can be used as bidentate ligands, the coordination abilities of 5, 6, and 8 were tested by the reaction with copper nitrate trihydrate, yielding the copper complexes trans-[diaquabis{1-(2-hydroxyethyl)-5-nitriminotetrazolato-kappa(2)N(4),O(5)}copper(II)] (14), trans-[diaquabis{1-(2-chloroethyl)-5-nitriminotetrazolato-kappa(2)N(4),O(5)}copper(II)] dihydrate (15), and [diaquabis{1-(2-azidoethyl)-5-nitriminotetrazolato-kappa(2)N(4),O(5)}copper(II)] (16). All compounds were characterized by low-temperature single-crystal X-ray diffraction. In addition, comprehensive characterization (IR, Raman, and multinuclear NMR spectroscopy ((1)H, (13)C), elemental analysis, mass spectrometry, DSC) was performed. The heats of formation of selected compounds were computed by using heats of combustion obtained by bomb calorimetry or calculated by the atomization method. With these values and the densities determined from X-ray crystallography, several detonation parameter were calculated by the EXPLO5 program. Finally, the sensitivities towards impact and friction were determined using a BAM drop hammer and friction tester.

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An X-Ray Study of Symmetrical Trinitrotoluene and Cyclo Trimethylenetrinitramine

Cited by 23 publications

References 0 publications

Topological pressure-temperature state diagram of the crystalline dimorphism of 2,4,6-trinitrotoluene

Topological pressure-temperature state diagram of the crystalline dimorphism of 2,4,6-trinitrotoluene

Redetermination ofcyclo-trimethylenetrinitramine

New Energetic Materials: Functionalized 1‐Ethyl‐5‐aminotetrazoles and 1‐Ethyl‐5‐nitriminotetrazoles

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