Diazoamination: A simple way to enhance detonation performance of aminoaromatic and aminoheterocyclic energetic materials

• Published in: FirePhysChem (Online) Vol. 1; no. 2; pp. 97 - 102
• Main Author: Bondarchuk, Sergey V.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-06-2021; KeAi Communications Co. Ltd
• Subjects: DFT; HEDM; Nitrogen-rich compound; Triazene; DFT; Triazene; Nitrogen-rich compound; HEDM
• ISSN: 2667-1344; 2667-1344
• DOI: 10.1016/j.fpc.2021.05.001

•Diazoamination reaction as a tool for molecular engineering of explosives is studied.•A quantitative description of the transformation efficiency is done for the general case.•An average enhancement of the detonation velocity (2-15%) and pressure (0-32%) is found.•Ten energetic triazenes with outstanding detonation properties are proposed.
In this paper, we report a theoretical study of the change in detonation efficiency of energetic amines undergone diazoamination reaction. For this purpose, we selected 17 aminoaromatic and aminoheterocyclic energetic materials, both widely known and newly synthesized, and ranked all possible triazenes derived from them according to our recently developed compositional criterion evaluation algorithm. Then, top ten structures were calculated using quantum-chemical methods to obtain more accurate estimates of their detonation properties, which were calculated using the Kamlet-Jacobs equations. To ensure that input parameters, namely, crystal density (dc) and enthalpy of formation (ΔHf) are correct, we have benchmarked a number of experimentally known triazenes as well as other structurally similar compounds. As a result, we have obtain good regression coefficients, R2 = 0.91 (for dc) and R2 = 0.96 (for ΔHf). Applying the same quantum-chemical methods for structural building blocks (constituents of triazenes) we have found that diazoamination always increases detonation performance (2-15% for detonation velocity and 0-32% for pressure). Thus, transformation of aminoaromatic and aminoheterocyclic energetic materials into triazenes is a convenient method for enhancement of their detonation properties.
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