Computational studies on two novel energetic nitrogen‐rich compounds based on tetrazolone

Abstract

Two novel energetic nitrogen‐rich compounds 1,4‐diaminotetrazol‐5‐one (DATO) and 1,4‐dinitrotetrazol‐5‐one (DNTO) were proposed first and studied by quantum chemistry method with B3LYP/6‐31G* level of theory. The optimized geometry, IR predicted spectrum and thermochemical parameters, frontier molecular orbitals and molecular electrostatic potential were calculated for inspecting the electronic structure, molecular stability and chemical reactivity. The important macroscopic properties including density, enthalpy of formation, detonation parameters and impact sensitivity have been predicted as well. As a result, two designed compounds DATO and DNTO possess positive enthalpy of formation (395.79 and 342.77 kJ/mol), impressive detonation parameters (D = 8.80 km/s, P = 33.69 GPa; D = 8.89 km/s, P = 34.98 GPa) superior to the remarkable explosive RDX, acceptable sensitivities and might be promising candidates of energetic materials. Copyright © 2015 John Wiley & Sons, Ltd.

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

“…Compounds 10, 16, 17, and 24 have higher V D than that of high-energy explosive ONC (9.50 km/s) and 17 has a value of P D comparative to explosive CL-20 (44.10 GPa). Results show that compounds 6,10,11,12,15,16,17,22,23, and 24 own better performance than widely used explosive HMX and may serve as promising candidates of environmentally friendly HEDMs.…”

“…For substituted tetrazolones (1)(2)(3)(4)(5)(6)(7), all N atoms of rings are in the same plane and bonding angles of the ring are about 108°. For tetrazolone derivatives with the linkage of -NH-(8-13) and -NHNH- (14)(15)(16)(17)(18)(19), the N atoms are not coplane and the bond lengths of C═O are about 1.208 Å. The remaining tetrazolone derivatives (20)(21)(22)(23)(24)(25) show centrosymmetric configurations with double tetrazolones linked by the azo bond and 2 substituted groups crossed arranged around the rings.…”

“…All the tetrazolone-based compouds FIGURE 4 Overall performance of tetrazolone-based compounds (TOs) compared with RDX and HMX in this work except 5, 7, 8, and 14 have similar or even better detonation properties compared to HMX, which is one of the most commonly used high-performance energetic ingredients. Compound 6,10,11,15,16,17,22,23, and 24 own excellent performance with detonation velocity of about 9.5 km/s and detonation pressure of about 41.0 GPa making them potential candidates of new green HEDMs.…”

“…[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. [15][16][17] Recent researches indicate high-nitrogen content and appropriate source of oxygen (O-NO 2 , N-NO 2 , C-NO 2 , N-O, etc) in the molecular skeleton can enhance oxygen balance and density, which further promote their detonation performance (detonation pressure and velocity). [18] In this paper, versatile tetrazolone-based compounds with some promising characteristics were designed (Scheme 1).…”

“…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. …”