Bis[3-(5-nitroimino-1,2,4-triazolate)]-Based Energetic Salts: Synthesis and Promising Properties of a New Family of High-Density Insensitive Materials

Wang, Ruihu; Xu, Hongyan; Guo, Yong; Sa, Rongjian; Shreeve, Jean’ne M.

doi:10.1021/ja1055033

Cited by 286 publications

(258 citation statements)

References 18 publications

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“…In the following, the structural characteristics of these compounds will be discussed in detail in comparison to the recently published symmetric bistriazoles. and hence well below the corresponding symmetric dinitro-(1.902 Å 3 ) 27 and dinitrimino (1.772 Å 3 ) 23 compound. As expected, the bistriazole moiety shows a completely planar assembly due to the electron delocalization in the molecule, the nitrimino moiety is pointing towards the nitrogen atom N5 and participates in an intramolecular hydrogen bond N5-H5⋯O3 with a D⋯A length of 2.619(3) Å and a D-H⋯A angle of 103(2)°.…”

Section: Single Crystal X-ray Structure Analysismentioning

confidence: 82%

Asymmetrically substituted 5,5′-bistriazoles – nitrogen-rich materials with various energetic functionalities

2013

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In this contribution the synthesis and full structural and spectroscopic characterization of three asymmetrically substituted bis-1,2,4-triazoles, along with different energetic moieties like amino, nitro, nitrimino and azido moieties, is presented. Additionally, selected nitrogen-rich ionic derivatives have been prepared and characterized. This comparative study on the influence of these energetic moieties on structural and energetic properties constitutes a complete characterization including IR, Raman and multinuclear NMR spectroscopy. Single crystal X-ray crystallographic measurements were performed and provide insight into structural characteristics as well as inter-and intramolecular interactions. The standard enthalpies of formation were calculated for all compounds at the CBS-4M level of theory, revealing highly positive heats of formation for all compounds. The detonation parameters were calculated using the EXPLO5 program and compared to the common secondary explosive RDX as well as recently published symmetric bistriazoles. As expected, the measured sensitivities to mechanical stimuli and decomposition temperatures strongly depend on the energetic moiety of the triazole ring. All compounds were characterized in terms of sensitivities (impact, friction, electrostatic) and thermal stabilities, the ionic derivatives were found to be thermally stable, insensitive compounds.

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Section: Single Crystal X-ray Structure Analysismentioning

confidence: 82%

Asymmetrically substituted 5,5′-bistriazoles – nitrogen-rich materials with various energetic functionalities

2013

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“…The structures of DADNP, TBADNP and DNADNP were optimized using Gaussian 09 in order to obtain their stable geometric configuration, and their densities were then calculated [15]. The densities of DADNP (1.85 g·cm −3 ), TBADNP (1.91 g·cm −3 ) and DNADNP (1.92 g·cm −3 ) fall in the range for high-performance energetic materials (1.8-2.0 g·cm −3 ) [23] and are superior to that of RDX (1.82 g·cm −3 ).…”

Section: Properties Of the Compoundsmentioning

confidence: 99%

Synthesis and Property of 1,4-Diamino-3,6-dinitropyrazolo[4,3-c]pyrazole and Its Derivatives

Li¹,

Wang²,

Shu³

et al. 2016

Cent. Eur. J. Energ. Mater.

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A synthetic procedure has been developed for the synthesis of 1,4-diamino-3,6-dinitropyrazolo[4,3-c]pyrazole (DADNP) via N-amination reaction. Its derivatives, 4,4'-(triaz-1-ene-1,3-diyl)bis (1-amine-3,6-dinitropyrazolo[4,3-c] pyrazole) (TBADNP) and 1,4-dinitramino-3,6-dinitropyrazolo[4,3-c]pyrazole (DNADNP), were first designed and synthesized by the diazotization and nitrification of amino group, and their structures were characterized by IR, 1 H NMR, 13 C NMR, elementary analysis and MS. The thermal properties of target compounds were studied by means of differential scanning calorimetry (DSC) and thermogravimetry (TG). The thermal decomposition peak temperatures of DADNP, TBADNP and DNADNP are 227, 236 and 288 °C, respectively. Results show that the derivatives of 1,4-diamino-3,6-dinitropyrazolo[4,3-c]pyrazole have better thermal stability.

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“…[8] However, low sensitivity and high performance are contradictory making the development of new HEDMs an interesting but challenging problem. [9] Nitrogen-rich heterocycles represent a unique class of energetic frameworks featuring a large number of energetic NN bonds, planar structures with electronic delocalization, and releasing environmentally friendly N 2 when decomposition or degradation. [10][11][12][13][14] Of these nitrogen-rich heterocycles, tetrazolone possesses high nitrogen and oxygen content, positive HOF, and good stability, which can be used as a building block in the design of new energetic compounds.…”

Section: Introductionmentioning

confidence: 99%

Computational design of tetrazolone‐based high‐energy density energetic materials: Property prediction and decomposition mechanism

Shi

2017

J of Physical Organic Chem

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The density functional theory methods are used to design a series of new highly energetic tetrazolone-based molecules by the combination of the linked tetrazolone framework and versatile substitutes. The molecular and electronic structures, physicochemical, and energetic properties were analyzed and predicted. The decomposition mechanisms were computationally simulated, and 3 potential decomposition channels were proposed. These newly designed tetrazolone-based compounds show high densities (up to 2.08 g/cm 3 ) and highly positive heats of formation (407.0-1377.9 kJ/mol) due to all right content of nitrogen and oxygen. Most of them exhibit good detonation velocity (8.31-9.62 km/s) and detonation pressure (32.40-43.86 GPa), and some are comparative to excellent explosive 10,11,12,15,16,17,22,23, and 24 own superior detonation performance than widely used explosive HMX and may be promising candidates of green high-performance energetic materials.

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Bis[3-(5-nitroimino-1,2,4-triazolate)]-Based Energetic Salts: Synthesis and Promising Properties of a New Family of High-Density Insensitive Materials

Cited by 286 publications

References 18 publications

Asymmetrically substituted 5,5′-bistriazoles – nitrogen-rich materials with various energetic functionalities

Asymmetrically substituted 5,5′-bistriazoles – nitrogen-rich materials with various energetic functionalities

Synthesis and Property of 1,4-Diamino-3,6-dinitropyrazolo[4,3-c]pyrazole and Its Derivatives

Computational design of tetrazolone‐based high‐energy density energetic materials: Property prediction and decomposition mechanism

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