High Density Energetic Zwitterionic Diazonium 1,2,4‐Triazolate Resulting from an Interesting Bond Cleavage of E‐1,2‐Bis(3,4‐diamino‐1,2,4‐triazol‐5‐yl)‐ethane

Abstract

An energetic zwitterion 5‐diazonium‐3‐trinitromethyl‐1,2,4‐triazolate (DTNMTz) was synthesized by an interesting bond cleavage of E‐1,2‐Bis(3,4‐diamino‐1,2,4‐triazol‐5‐yl)‐ethane. Its structure was confirmed by single‐crystal X‐ray diffraction. The physicochemical properties such as electrostatic potential, thermal properties and sensitivity towards impact, friction and electrostatic discharge were evaluated. Its heat of formation, detonation pressure and velocity were calculated. It is worth noting that this zwitterion behaves zero CO2 oxygen balance, and it has high density at ambient temperature (1.89 g cm−3), considerable detonation performance (D: 9317 m s−1, P: 37.6 GPa).

A zwitterionic fused-ring framework as a new platform for heat-resistant energetic materials

“…On the other hand, the bond distances between N4 and C3 as well as N4 and C4 are 1.333 (1) Å and 1.338 (1) Å, respectively, representing typical bond lengths of the C sp 2 -N sp 3 single bond. 47,48 In addition, X-ray diffraction analysis and 1 H NMR spectroscopy of ZDPT suggest that no bonding of N10 with other atoms was observed, indicating that the negative charge of ZDPT is concentrated on the N10 atom. These ndings support the zwitterionic structure of ZDPT.…”

C6N10O4: Thermally Stable Nitrogen-Rich Inner Bis(diazonium) Zwitterions

“…Unlike photosensitive DDNP, neither 2 nor 4 is sensitive to light even after exposure to ambient light for 4 weeks. Compound 4 has comparable decomposition temperature (150 °C) with traditional primary explosive DDNP (157 °C) . While compound 2 decomposes at 199 °C (Figure S8, Supporting Information), which is much higher than 4 and some other reported proton-free nitrogen-rich diazonium salts. ,, The heats of formation of 2 and 4 were calculated to be 819.7 and 987.2 kJ mol –1 , respectively, which is much higher than that of DDNPz.…”

“…They can be used as valuable building blocks or intermediates in a wide range of organic syntheses . In general, the synthesis of a diazonium salt is initiated by the diazotization of an aromatic amine with sodium nitrite and a mineral acid or in an organic solvent using an alkyl nitrite reagent. − Some of them are prepared by the nitration in a mixed acid. − With the development of isolation technology and characterization methods, many more diazonium salts have been isolated and confirmed by their solid state structures. Nevertheless, the diazonium salts are most generally used in situ without isolation due to their extremely dangerous nature rising from low thermal stability and chemical instability.…”

Synthesis of (5-Iminio-4,5-dihydro-1,3,4-oxadiazol-2-yl)tetrazol-1-ide: A Zwitterionic Compound Containing a Tetrazole Anion as a Promising Blunt Energetic Material

“…11 The formation of zwitterionic compounds is another effective way to improve the safety of energetic materials. Over the past years, there has been sustained research activity in zwitterionic compounds, such as zwitterionic compounds related to tetrazine dioxides 12 , tetrazazpentalenes 13 , and triazoles [14][15][16][17][18] . Studies have shown that zwitterionic energetic materials can improve performance by increasing density and stability through electrostatic interactions within the same molecule.…”

“…Over the past years, there has been sustained research activity in zwitterionic compounds, such as zwitterionic compounds related to tetrazine dioxides, 12 tetrazazpentalenes, 13 and triazoles. [14][15][16][17][18] Studies have shown that zwitterionic energetic materials can improve performance by increasing density and stability through electrostatic interactions within the same molecule. 14,15 Zwitterionic compounds are electronically neutral and carry both positive and negative charges in the same molecule.…”