Improving the stability of hydrazinium pentazolate through cocrystallization

Zhou, Jianxin; Hou, Tianyang; Xu, Zhihong; Wang, Pengcheng; Lu, Ming; Xu, Yuangang

doi:10.1039/d2ce01707e

Cited by 9 publications

(4 citation statements)

References 31 publications

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“…30,31 Under impact loading at moderate levels, PZDO actively reacts, as evidenced by sooty deposits (Figure S2, Supporting Information) and smoke. The decomposition is a positive event by STANAG4489 protocol; thus, the impact 16 barbituric acid, 17 carbamazepine, 17 4-hydroxybenzamide monohydrate 17 ) and with energetic coformers (ethylenedinitramine, 7 ammonium dinitramide, 11 5-(nitrimino)-1H-tetrazole, 10 1-methyl-5-(nitrimino)-1H-tetrazole, 10 4,4′,5,5′-tetranitro-2,2′-biimidazole, 18 3,6-dinitropyrazolo[4,3-c]pyrazole, 9 3nitro-1,2,4-triazol-5-one, 9 hydrazinium cyclo-pentazolate, 19 and those found in present study, viz., with 3,4-dinitropyrazole and 3,5-dinitropyrazole). sensitivity has been obtained in full series as the drop energy corresponding to 50% probability of initiation.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Cocrystals of PZDO deposited in the Cambridge Structural Database with nonenergetic coformers (trimesic acid, barbituric acid, carbamazepine, 4-hydroxybenzamide monohydrate) and with energetic coformers (ethylenedinitramine, ammonium dinitramide, 5-(nitrimino)-1 H -tetrazole, 1-methyl-5-(nitrimino)-1 H -tetrazole, 4,4′,5,5′-tetranitro-2,2′-biimidazole, 3,6-dinitropyrazolo[4,3- c ]pyrazole, 3-nitro-1,2,4-triazol-5-one, hydrazinium cyclo-pentazolate, and those found in present study, viz., with 3,4-dinitropyrazole and 3,5-dinitropyrazole).…”

Section: Introductionmentioning

confidence: 99%

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Pyrazine 1,4-Dioxide is a Prolific Cocrystal Former and Energetic Material Itself

Monogarov,

Melnikov,

Vatsadze

et al. 2024

Crystal Growth & Design

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Pyrazine 1,4-dioxide (PZDO) is a chemical frequently employed as a coformer in cocrystal design. It has two Noxide fragments that signify potential hazards, but we found no information about it in prior literature. Therefore, we investigate the thermal behavior, thermochemical properties, and mechanical sensitivity of the title compound. We demonstrate that the material explodes in standard impact tests at a certain drop energy. By the level of its computed energetic potential, PZDO approaches benchmark trinitrotoluene. We screened ten energetic materials for cocrystal formation with PZDO using thermal analysis methods and predicted three novel cocrystals. However, we failed to grow the X-ray quality crystals by the conventional approach due to significantly differing solubility of PZDO and other components in common solvents. Two suitable coarse cocrystals of 3,4-dinitropyrazole/PZDO and 3,5-dinitropyrazole/PZDO were finally prepared by resublimation (vacuum recondensation of preformed comelt), and its X-ray structure is reported. Overall, we characterize PZDO as an energetic material and highlight the potential risks associated with the compound. The preparation of cocrystals via the gas phase route, although laborious, may be effective when the traditional (via solution) approach fails.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pyrazine 1,4-Dioxide is a Prolific Cocrystal Former and Energetic Material Itself

Monogarov,

Melnikov,

Vatsadze

et al. 2024

Crystal Growth & Design

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“…The complex of ammonium dinitramide (ADN) pyrazine-1,4-dioxide (PDO) showed ADN/PDO had a higher melting point and decomposition temperature than ADN . And the application of the polynitrogen compound was the complex of 3,6,7-triamino-7 H -[1,2,4]triazolo[4,3- b ][1,2,4]triazol-2-ium pentazolate with 3,6,7-triamino-7 H -[1,2,4]triazolo[4,3- b ][1,2,4]triazole (HTATOTN 5 /TATOT) and hydrazinium pentazolate (N 2 H 5 N 5 ) with PDO, which also were with higher decomposition temperature. , …”

Section: Introductionmentioning

confidence: 99%

“…20 And the application of the polynitrogen compound was the complex of 3,6,7triamino-7H- [1,2,4]triazolo [4,3-b] [1,2,4]triazol-2-ium pentazolate with 3,6,7-triamino-7H- [1,2,4]triazolo [4,3-b][1,2,4]triazole (HTATOTN 5 /TATOT) and hydrazinium pentazolate (N 2 H 5 N 5 ) with PDO, which also were with higher decomposition temperature. 21,22 Therefore, based on the stable azide anion and pentazolate anion, this work theoretically explores the molecular structures and crystal structures of six neutral polynitrogen compounds N 6 (1−3), N 8 (4,5) various aspects, including calculation of electronic structures, analysis of wave functions, kinetic simulation of crystal structures, and calculation of thermal decomposition transition states. The main research contents include the optimized geometry, the property of bond, AIM theory, 23 deformation of electron density, 24 aromaticity analysis, the decomposition product of the crystal structures simulated by ab initio molecular dynamics (AIMD), and the calculation of thermal decomposition transition states.…”

Section: Introductionmentioning

confidence: 99%

Enhancing Stability in Polynitrogen Compounds: Mechanisms and Strategies

Jiang,

Wang,

et al. 2023

Crystal Growth & Design

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Polynitrogen energetic materials have become an important branch of high-energy-density materials. In this work, a theoretical exploration of structures and thermal stability in polynitrogen compounds N6, N8, and N10 was conducted based on synthesized azide and pentazolate compounds. By employing wave function analyses and kinetic simulations, the equilibrium geometries, properties of bonds, and indices to represent aromaticity were explored and represented. In addition, their crystal structures were predicted, and the decomposition processes and products of ab initio molecular dynamics (AIMD) simulations and transition-state calculations were carried out. Moreover, their decomposition barrier can be significantly increased by forming complexes with HMX and CL-20. Compounds HMX–1, HMX–4, CL-20–1, and CL-20–4 showed satisfactory thermal stability compared with pentazolate salts. These research results provide theoretical support and possibilities for the synthesis of polynitrogen compounds.

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Insight into the Stability of Pentazolyl Derivatives based on Covalent Bond

Jiang,

Xia,

Zhang

et al. 2024

ChemPhysChem

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Pentazole is regarded as a unique inorganic molecule that possess organic heterocyclic structure. Therefore, the research on pentazolyl derivatives represents a cutting‐edge direction in both contemporary inorganic chemistry and heterocyclic chemistry. Moreover, their synthesis is regarded as the most significant research topic in the field of energetic materials due to the great potential of pentazolyl derivatives to breakthrough the energy bottleneck of CHNO‐based energetic materials. However, synthesizing pentazolyl derivatives is challenging. To provide a theoretical support for the synthesis, we conducted theoretical studies on six single‐ring pentazolyl derivatives with different functional groups. The results suggest that derivatization reduces the bond strength and weakens the aromaticity of the pentazolate ring. Further analysis showed that derivatization mainly affects the π aromaticity of the pentazolate ring, and ultimately causing poor stability of the pentazolyl derivatives. Among the six derivatives investigated in this study, fluoro pentazole (cyclo‐N5‐F) and hydroxyl pentazole (cyclo‐N5‐OH) possess good aromaticity, which is similar to the reported cyclo‐N5‐NCHN(CH3)2. Further calculations show that the kinetic stability of cyclo‐N5‐OH is higher than that of cyclo‐N5‐F. These results collectively indicate that cyclo‐N5‐OH is a promising candidate for synthesizing single‐ring pentazolyl derivatives.

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Improving the stability of hydrazinium pentazolate through cocrystallization

Abstract: An energetic cocrystal of hydrazinium cyclo-pentazolate and pyrazine-1,4-dioxide (2:1), N2H5N5/PDO, was synthesized. The cocrystal, as characterized by single-crystal X-ray diffraction, IR, Raman, XRD, and elemental analysis, has higher density, lower...

Cited by 9 publications

References 31 publications

Pyrazine 1,4-Dioxide is a Prolific Cocrystal Former and Energetic Material Itself

Pyrazine 1,4-Dioxide is a Prolific Cocrystal Former and Energetic Material Itself

Enhancing Stability in Polynitrogen Compounds: Mechanisms and Strategies

Insight into the Stability of Pentazolyl Derivatives based on Covalent Bond

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