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, cilt.1205, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1205
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.molstruc.2019.127580
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Picric acid, Impact sensitivity, Energetic salts, HOMO-LUMO gaps, pi...pi stacking, Detonation performance, INTERMOLECULAR INTERACTIONS, PI-STACKING, LOW-SENSITIVITY, HYDROGEN-BOND, CRYSTALS, COCRYSTAL, DENSITY, PACKING, DESIGN, GROWTH
  • Ankara Üniversitesi Adresli: Evet

Özet

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 pi...pi 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 center dot center dot center dot H, O center dot center dot center dot H, O center dot center dot center dot O, N center dot center dot center dot H and C center dot center dot center dot C (pi...pi) 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 p-stacking constructed by large pi-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. (C) 2019 Elsevier B.V. All rights reserved.