Nitroamino Triazoles: Nitrogen‐Rich Precursors of Stable Energetic Salts

Huang, Yangen; Gao, Haixiang; Twamley, Brendan; Shreeve, Jean’ne M.

doi:10.1002/ejic.200800160

Cited by 74 publications

(58 citation statements)

References 69 publications

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“…[7] A large number of nitrogen-rich salts have been explored by chemists in Idaho, Germany, and other groups around the world. [8][9][10] Among these salts nitroamino compounds, such as those based on 5-nitroaminotetrazole, [10a, 11, 12] 3amino-6-nitroamino-tetrazine, [13] 4-nitroamino-1,2,4-triazole, and 1-nitroamino-1,2,3-triazole, [14] exhibit excellent performance in terms of impact and friction sensitivity, and detonation velocity and pressure. The presence of the nitroamino group greatly improves the oxygen balance and density.…”

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confidence: 99%

3‐Azido‐N‐nitro‐1H‐1,2,4‐triazol‐5‐amine‐Based Energetic Salts

Wang

Parrish

Shreeve

2011

Chemistry A European J

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Twelve energetic nitrogen-rich salts based on 3-azido-N-nitro-1H-1,2,4-triazol-5-amine were prepared and fully characterized by (1)H, (13)C NMR, and IR spectroscopy, differential scanning calorimetry (DSC), and elemental analysis. The crystal structures of the neutral compound 3-azido-N-nitro-1H-1,2,4-triazole-5-amine (1) and its triaminoguanidinium salt (13) were determined by single-crystal X-ray diffraction. The density of 1 and its twelve salts ranged from 1.57 to 1.79 g cm(-3), and the heat of formation was calculated with the Gaussian 03 suite of programs. Compounds 1-13 exhibit promising detonation performances (pressure: 25.3-39.3 GPa; velocity: 8159-9409 m s(-1); EXPLO 5.05). Impact sensitivities were also determined by hammer tests and resulted ranging from 2.5 J (very sensitive) to >40 J (insensitive).

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confidence: 99%

3‐Azido‐N‐nitro‐1H‐1,2,4‐triazol‐5‐amine‐Based Energetic Salts

Wang

Parrish

Shreeve

2011

Chemistry A European J

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“…As shown in Table 1, all of the salts decomposed without melting, and the decomposition temperatures of salts 1 – 9 fall in the range 143.2 ( 2 ) to 178.8 °C ( 8 ), which are all higher than the neutral precursor DNAP ( T d = 121 °C). Salt formation is usually an efficient method for improving thermal stability,20,21 and this is also the case for DNAP‐based salts. The decomposition of explosives may be caused by the reactions within or between molecules at a specific temperature.…”

Section: Resultsmentioning

confidence: 99%

2‐(Dinitromethylene)‐1‐nitro‐1, 3‐diazacyclopentane‐Based Energetic Salts

Song

Zhou

Cao

et al. 2012

Zeitschrift anorg allge chemie

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Energetic salts that contain nitrogen‐rich cations and the 2‐(dinitromethyl)‐3‐nitro‐1, 3‐diazacyclopent‐1‐ene anion were synthesized in high yield by direct neutralization reactions. The resulting salts were fully characterized by multinuclear NMR spectroscopy (1H and 13C), vibrational spectroscopy (IR), elemental analysis, density and differential scanning calorimetry (DSC), and elemental analysis. Additionally, the structures of the ammonium (1) and isopropylideneaminoguanidinium (9) 2‐(dinitromethyl)‐3‐nitro‐1, 3‐diazacyclopent‐l‐ene salts were confirmed by single‐crystal X‐ray diffraction. Solid‐state 15N NMR spectroscopy was used as an effective technique to further determine the structure of some of the products. The densities of the energetic salts paired with organic cations fell between 1.50 and 1.79 g·cm–3 as measured by a gas pycnometer. Based on the measured densities and calculated heats of formation, detonation pressures and velocities were calculated using Explo 5.05 and found to to be 25.2–35.5 GPa and 7949–9004 m·s–1, respectively, which make them competitive energetic materials.

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“…[47][48][49][50] However,t hey have also turned to less usual methods, such as G2 or G2 MP2, [51][52][53][54] or more advanced methods, such as G3 and G3MP2, [53,55] and CBS variants. [53] Typically,t hese authors use composite methods, especially G2 or G2MP2, for protonation [54,[56][57][58][59][60][61][62][63][64] or atomization [65][66][67][68][69][70][71] reactions.…”

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confidence: 99%

Energetic Properties of Rocket Propellants Evaluated through the Computational Determination of Heats of Formation of Nitrogen‐Rich Compounds

Forquet

Sabaté

Chermette

et al. 2016

Chemistry An Asian Journal

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The use of ab initio and DFT methods to calculate the enthalpies of formation of solid ionic compounds is described. The results obtained from the calculations are then compared with those from experimental measurements on nitrogen-rich salts of the 2,2-dimethyltriazanium cation (DMTZ) synthesized in our laboratory and on other nitrogen-rich ionic compounds. The importance of calculating accurate volumes and lattice enthalpies for the determination of heats of formation is also discussed. Furthermore, the crystal structure and hydrogen-bonding networks of the nitroformate salt of the DMTZ cation is described in detail. Lastly, the theoretical heats of formation were used to calculate the specific impulses (Isp ) of the salts of the DMTZ cation in view of a prospective application in propellant formulations.

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Nitroamino Triazoles: Nitrogen‐Rich Precursors of Stable Energetic Salts

Cited by 74 publications

References 69 publications

3‐Azido‐N‐nitro‐1H‐1,2,4‐triazol‐5‐amine‐Based Energetic Salts

3‐Azido‐N‐nitro‐1H‐1,2,4‐triazol‐5‐amine‐Based Energetic Salts

2‐(Dinitromethylene)‐1‐nitro‐1, 3‐diazacyclopentane‐Based Energetic Salts

Energetic Properties of Rocket Propellants Evaluated through the Computational Determination of Heats of Formation of Nitrogen‐Rich Compounds

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