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


Sen N., NAZIR H., Atceken N., Hope K. S., ACAR N., ATAKOL O.

Journal of Molecular Structure, vol.1205, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1205
  • Publication Date: 2020
  • Doi Number: 10.1016/j.molstruc.2019.127580
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Police Academy Affiliated: Yes

Abstract

© 2019In 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.