Energetic Triazolotriazines with Trifluoromethyl, Dinitromethyl and Nitroamino Groups: Synthesis, Structure and Properties

Abstract

A series of energetic triazolotriazines 6-11 with dinitromethyl, trifluoromethyl and/or nitroamino groups were synthesized via cyclization, amidoximation, chlorination and nitration starting from aminoguanidine bicarbonate. All compounds were thoroughly characterized by nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR), mass spectrometry (MS), and differential scanning calorimetry (DSC). The crystal structures of compounds 9, 10, and 11 were further studied by single-crystal X-ray dif-fraction analysis. The physicochemical and detonation properties of 6-11 were investigated. Generally, compounds 6–8 have a high density of 1.873-2.047 g·cm⁻³ and a good detonation performance (D: 8025-8262 m·s⁻¹ and P: 27.3-29.3 GPa). Additionally, com-pounds 6, 9, and 10 exhibit a low sensitivity (IS ≥ 40 J and FS: 120-240 N). Non-covalent interac-tion (NCI), 2D fingerprint plots, and Hirshfeld sur-face analysis were em-ployed to investigate the intermolecular interaction.