Energetic multifunctionalized nitro/nitramino isomeric pyrazole–tetrazole hybrids: enhancing density and detonation properties through hydrogen bonding and π–π interactions

Thaltiri, Vikranth; Staples, Richard J.; Shreeve, Jean'ne M.

doi:10.1039/d4ta03084b

J. Mater. Chem. A

2024

DOI: 10.1039/d4ta03084b

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Energetic multifunctionalized nitro/nitramino isomeric pyrazole–tetrazole hybrids: enhancing density and detonation properties through hydrogen bonding and π–π interactions

Vikranth Thaltiri,

Richard J. Staples,

Jean'ne M. Shreeve

Abstract: This study focuses on synthesizing high-density isomeric pyrazole-tetrazoles and their energetic salts, with a particular emphasis on improving detonation performance. First synthesized was 5-(3,4-dinitro-1H-pyrazol-5-yl)-1H-tetrazole (H2DNP-5T, 3), an isomer of 5-(3,4-dinitro-1H-pyrazol-5-yl)-1H-tetrazole...

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Cited by 4 publications

References 38 publications

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Energetic Nitrated Azole Assemblies: Linear Alliance of Isomeric Furazan-1,2,4-triazole-pyrazole Combinations

Dalinger,

Khoranyan,

Suponitsky

et al. 2024

Crystal Growth & Design

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While the effect of isomerism on the properties of energetic molecules has long been recognized, the use of this phenomenon to deliberately improve the performance of energetic materials has now been approached. Here, we report the development of effective protocols for the preparation of isomeric energetic compounds with a furazan-triazole-pyrazole framework, which differ in the binding points of these subunits and in the position of the nitro group. The two synthesized isomers readily form X-ray quality crystals of solvates with DMSO and water, but only one isomer was able to give unsolvated crystals. Significant differences in molecular geometry and noncovalent interactions due to the effect of the solvent incorporated into the crystal lattice are highlighted. The ambiguity of evaluating structure−property relationships for a single compound from the X-ray data of its solvate is demonstrated. The isomer synthesized for the first time, 3-(5-(5-(3,4-dinitro-1H-pyrazol-5-yl)-1H-1,2,4-triazol-3-yl)-4-nitrofurazan (6), is of greater interest because, unlike the other isomer, it is not hygroscopic and has a higher density. Isomer 6 has a shock sensitivity and detonation velocity similar to those of RDX, but it is more thermally stable and insensitive to friction.

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Energetic Nitrated Azole Assemblies: Linear Alliance of Isomeric Furazan-1,2,4-triazole-pyrazole Combinations

Dalinger,

Khoranyan,

Suponitsky

et al. 2024

Crystal Growth & Design

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Tailoring the Energetic Properties of Pyrazole Hybrids through Functionalization with Dinitromethyl and N-Hydroxytetrazole

Thaltiri,

Staples,

Shreeve

2024

J. Org. Chem.

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The functionalization of pyrazole-based compounds with dinitromethyl and N-hydroxytetrazole groups resulted in enhanced energetic properties. Two key compounds, 5-(dinitromethyl)-3,4-dinitro-1H-pyrazole ( 5) and 5-(3,4-dinitro-1H-pyrazol-5-yl)-1H-tetrazol-1-ol (7), along with their salts, were synthesized and evaluated for their energetic properties. Notably, the bishydroxylammonium salts 5b (D v : 8778 m•s −1 ; P: 33.1 GPa) and 7b (D v : 8988 m•s −1 ; P: 34.6 GPa) demonstrated an optimal balance between high detonation performance, good thermal stability, and low sensitivity, outperforming RDX, and positioning them as promising candidates for advanced secondary energetic materials.

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Construction of heterocycle-triazolotriazine framework energetic compounds: towards novel high-performance explosives

Yang,

Zheng,

Zhang

et al. 2024

Chem. Commun.

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Energetic multifunctionalized nitro/nitramino isomeric pyrazole–tetrazole hybrids: enhancing density and detonation properties through hydrogen bonding and π–π interactions

Cited by 4 publications

References 38 publications

Energetic Nitrated Azole Assemblies: Linear Alliance of Isomeric Furazan-1,2,4-triazole-pyrazole Combinations

Energetic Nitrated Azole Assemblies: Linear Alliance of Isomeric Furazan-1,2,4-triazole-pyrazole Combinations

Tailoring the Energetic Properties of Pyrazole Hybrids through Functionalization with Dinitromethyl and N-Hydroxytetrazole

Construction of heterocycle-triazolotriazine framework energetic compounds: towards novel high-performance explosives

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