DFT calculations on three novel compounds containing N12, N14 and N16 chains: DPyTD, DTrTD and DTeTD

• Three high nitrogen compounds with N12, N14 or N16 chains were studied using density functional theory.
• The calculated energies required for 1,3-dipolar cycloadditions show that syntheses of title compounds are possible.
• IR, UV and NMR spectra were simulated for characterization.
• The predicted impact sensitivities of title compounds are acceptable.

Three high nitrogen compounds, 1,2-di(5H-pyrazolo[1,5-d]tetrazol-5-yl)diazene (DPyTD), 1,2-di(6H-[1–3]triazolo[1,5-e]tetrazol-6-yl)diazene (DTrTD) and 1,2-di(3H-tetrazolo[1,5-e]tetrazol-3-yl)diazene (DTeTD) with N12, N14 or N16 chain produced by the internal 1,3-dipolar cycloadditions of bis(azidoazolyl)diazenes (1,2-bis(3-azido-1H-pyrazol-1-yl)diazene, 1,2-bis(4-azido-1H-1,2,3-triazol-1-yl)diazene and 1,2-bis(5-azido-1H-tetrazol-1-yl)diazene), were studied using the density functional theory (DFT). The energies (Ea,1 and Ea,2) required for the two internal cycloadditions of bis(azidoazolyl)diazenes were predicted at the B3LYP/6-311++G∗∗ (128.8–138.5 and 130.2–144.7 kJ/mol), B3PW91/6-311++G∗∗ (124.9–133.0 and 125.5–138.1 kJ/mol) and B3LYP/Aug-cc-pvdz (119.0–128.0 and 120.5–133.0 kJ/mol) levels of DFT. The bend of the azido group starts the 1,3-dipolar cycloadditions. Two 1,3-dipolar cycloadditions are independent. The IR, UV, and NMR spectra were simulated for characterization. The frontier orbitals cover the whole structure leading to small energy gaps (2.99–4.02 eV). The predicted impact sensitivities (17.3–22.1 J) show the acceptable stability of title compounds.

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