Tetranitro-diazinodiazines as high energy materials: computational investigation of structural aspects of fused heterocyclic backbone and isomerism

• Published in: Structural chemistry Vol. 32; no. 6; pp. 2175 - 2181
• Main Authors: Maan, Anjali, Ghule, Vikas Dasharath, Dharavath, Srinivas
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.12.2021; Springer Nature B.V
• Subjects: Backbone; Chemistry; Chemistry and Materials Science; Computer Applications in Chemistry; Density functional theory; Detonation; Energetic materials; Heat of formation; Investigations; Isomers; Nitrogen atoms; Nitrogen dioxide; Original Research; Physical Chemistry; Stability; Theoretical and Computational Chemistry; Diazinodiazine, Energetic materials; Heat of formation; Fused heterocycle; Detonation properties
• ISSN: 1040-0400; 1572-9001
• DOI: 10.1007/s11224-021-01791-1

Thirteen tetranitro-diazinodiazines have been designed and investigated to find the importance of diazinodiazine fused-heterocyclic backbone for energetic materials. The positional influence of four nitrogen atoms in the diazinodiazine backbone on the heat of formation, performance, and stability has been investigated by density functional theory. It is observed that diazinodiazine is an efficient backbone to improve energy content in the designed derivatives. The energy contribution from the diazinodiazine backbone varies from 352–558 kJ/mol. Introducing four –NO 2 groups into the diazinodiazine backbone resulted in new energetic molecules with acceptable detonation performance and stability. Their densities, detonation velocities, and detonation pressures were 1.87–1.89 g/cm 3 , 8.36–8.68 km/s, and 31.72–34.42 GPa, respectively. The bond dissociation energies for the longer C–NO 2 bonds fall in the range of 207–233 kJ/mol, reveals the stable nature of tetranitro-diazinodiazines. Thus, diazinodiazine isomers may be regarded as promising aromatic heterocyclic backbone, and tetranitro-diazinodiazines appear to be potential candidates for energetic materials. Graphical abstract