Nitrogen-Rich Bis-1,2,4-triazoles-A Comparative Study of Structural and Energetic Properties

• Published in: Chemistry : a European journal Vol. 18; no. 52; pp. 16742 - 16753
• Main Authors: Dippold, Alexander A., Klapötke, Thomas M.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 21.12.2012; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Comparative studies; energetic materials; heterocycles; nitrogen; NMR spectroscopy; Physical Sciences; Science & Technology; X-ray diffraction; ACID; heterocycles; HEATS; nitrogen; VII; X-ray diffraction; SET MODEL CHEMISTRY; energetic materials; NMR spectroscopy; SALTS; 2-NITROGUANIDINE DERIVATIVES; TRIAZOLES
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201202483

In this contribution, the synthesis and full structural and spectroscopic characterization of five bis‐1,2,4‐triazoles in combination with different energetic moieties like amino, nitro, nitrimino, azido, and dinitromethylene groups is presented. The main goal is a comparative study on the influence of those energetic moieties on the structural and energetic properties. A complete characterization including IR, Raman, and multinuclear NMR spectroscopy of all compounds is presented. Additionally, X‐ray crystallographic measurements were performed and deliver insight into structural characteristics as well as inter‐ and intramolecular interactions. The standard enthalpies of formation were calculated for all compounds at the CBS‐4M level of theory, the detonation parameters were calculated by using the EXPLO5.05 program. Additionally, the impact as well as the friction sensitivities and the sensitivity against electrostatic discharge were determined. The potential application of the synthesized compounds as energetic material will be studied and evaluated by using the experimentally obtained values for the thermal decomposition, the sensitivity data, and the calculated performance characteristics. Bang, boom, bang: In this contribution the synthesis and full structural and spectroscopic characterization of five bis‐1,2,4‐triazoles in combination with different energetic moieties like amino, nitro, nitrimino, azido, and dinitromethylene groups is presented (see figure). The main goal is a comparative study on the influence of those energetic moieties on structural and energetic properties.