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 using the starting materialaminoguanidine 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 diffraction analysis. The physicochemical and detonation properties of 6–11 were investigated. Generally, compounds 6–8 have high densities of 1.873–2.047 g cm⁻³ and good detonation performance (D: 8025–8262 m s⁻¹ and P: 27.3–29.3 GPa). Additionally, compounds 6, 9, and 10 exhibit low sensitivities (IS ≥ 40 J and FS: 120–240 N). Non-covalent interaction (NCI), 2D fingerprint plots, and Hirshfeld surface analysis were employed to investigate the intermolecular interactions.