Synthesis, characterisation and energetic performance of insensitive energetic salts formed between picric acid and 2,3-diaminotoluene, 2,4-diaminotoluene

In order to broaden the practical applications of Picric acid (PA), salts of PA have been synthesised with 2,3-diaminotoluene (PIC:23DAT), and 2,4-diaminotoluene (PIC:24DAT). This paper was discussed their synthesis, structural characterisation and supramolecular interactions. Salt formation was also observed between the phenolate hydrogen and amino groups. X-ray diffraction data shows that the salts are primarily formed through host-guest π … π stacking face-to-face interactions these non-covalent interactions govern the structures of the salts. Hirshfield surfaces and associated fingerprint plots of the salts were examined and the results indicated that the structures are stabilized by H⋯H, O⋯H, O⋯O, N⋯H and C⋯C (π … π) intermolecular interactions. The enthalpies of formation, the optimized structures, molecular total energies, frontier orbit energies, and HOMO-LUMO gaps of each compound were calculated using Gaussian 09; and detonation performances were calculated by using the EXPLO5 software. The results show that face-to-face π-stacking constructed by large π-bonded molecules and strong intra-intermolecular hydrogen bonding, which promote insensitivity in energetic materials. Both PIC:23DAT and PIC:24DAT salts were found to be approximately 80% less impact sensitive than PA. [Display omitted] •Energetic salts formation was observed between the phenolate hydrogen and amino groups.•Strong intra-intermolecular hydrogen bonding and face-to-face π-stacking, promote insensitivity in energetic salts.•Relationship between the crystal packing and impact sensitivity of energetic salts.•Structure analysis and characterisation of new formed energetic salts.•Visual analysis of short contacts was achieved through Hirshfeld surface analysis associated fingerprint plots.