Insights into the synthesis of hexaaminobenzene hydrochloride: An entry to hexaazatriphenylenes

Vázquez, Darián; Comba, María Betina; Spanevello, Rolando A.; Libonatti, Bernardo; Mangione, María Inés

doi:10.1016/j.molstruc.2022.132385

Cited by 1 publication

(1 citation statement)

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“…These backbones of N-heterocycles contain a large amount of NN bonds and CN bonds which endow themselves with a high heat of formation, resulting in their good detonation property. − In recent years, compounds characterized with vicinal amino/nitro functionalities have attracted wide attention for promising applications as advanced energetic materials. Typical energetic compounds of this kind, such as TATB and PTX (pyrazolo triazine explosive), have been widely used as a heat-resistant explosive or secondary explosive on the military aspect. Thus, further exploration of energetic compounds with vicinal amino/nitro functionalities has vital and practical significance.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of 1,2,4-Triazol-3-one-Based Energetic Compounds

Yang

Cheng

Tang

et al. 2022

Crystal Growth & Design

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1,2,4-Triazol-3-one (TO) is an important nitrogen-rich heterocycle in synthesis chemistry. In the field of energetic materials, some synthesis strategies are applied to prepare TO-derived energetic materials. However, none of them can be used as a heat-resistant energetic material due to their lower decomposition temperatures. In this paper, a series of energetic TO derivatives 4−13 were prepared from 5oxo-4,5-dihydro-1H-1,2,4-triazole-3-carboxylic acid. These compounds were fully characterized by using elemental analysis, 1 H and 13 C NMR spectroscopy, IR analysis, and MS. The crystal structures of fused-ring compound 6 and perchlorate 8 were further identified using single-crystal X-ray diffraction. Most compounds exhibit good thermostability (T d = 166.5−324.5 °C), low sensitivities (impact sensitivity IS ≥ 20 J; friction sensitivity FS ≥ 360 N), good detonation performance (D v = 7905−8753 m s −1 ), and positive heats of formation (ΔH f = 295.9−1121.1 kJ mol −1 ), except compound 9 (T d = 92 °C; IS = 15 J; FS = 240 N). Among these target molecules, compound 6 with a high decomposition temperature (T d = 324.5 °C), a high density (ρ = 1.859 g cm −3 ), low sensitivities (IS > 40 J; FS > 360 N), and a decent detonation performance (D v = 8406 m s −1 ; P = 29.2 GPa) is superior to the traditional heat-resistant explosive hexanitrostilbene (T d = 318 °C; ρ = 1.750 g cm −3 ; IS = 5 J; FS = 240 N; D v = 7612 m s −1 ; P = 26.3 GPa) and can be used as an insensitive and thermostable energetic material.

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