Harnessing triazole-oxadiazole-trinitromethyl moieties in the synthesis of insensitive energetic material with enhanced detonation performance

• Published in: New journal of chemistry 2024-08, Vol.48 (34), p.1486-14864
• Main Authors: Vangara, Srinivas, Kommu, Nagarjuna, Sahoo, Akhila K
• Format: Article
• Language: English
• Subjects: Chemical synthesis; Detonation; Energetic materials; Heat of formation; Nitrogen dioxide; NMR; Nuclear magnetic resonance; Oxadiazoles; Oxygen; PETN; Surface analysis (chemical); Topology; Triazoles
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/d4nj03052d

The nitrogen-and oxygen-rich azole-based high energetic compound 3,3′-(2-(trinitromethyl)-2 H -1,2,3-triazole-4,5-diyl)-bis(1,2,4-oxadiazole) ( 5 ) was synthesized from a readily accessible bis-cyano-substituted-azole in three steps with an overall good yield. The reaction sequence was even successful on the gram scale. The five-membered azole backbone with a -C(NO 2 ) 3 group contributes to boosting energetic properties of the molecule. The synthesized compounds were fully characterized using NMR, IR, HRMS, and TGA-DSC studies. X-ray diffraction analysis established the molecular topology of the desired compound. The molecule showed promising energetic performance with a good oxygen balance (−31.6%), high positive heat of formation (+679.8 kJ mol −1 ), and high detonation pressure ( P = 29.6 GPa) and velocity ( D v = 8356 m s −1 ), which are close to those of PETN, superior to those of HNS, and surpass those of TNT. Hirshfeld surface analysis gives insights into the molecule's sensitivity. The nitrogen-and oxygen-rich azole-based high energetic compound 3,3′-(2-(trinitromethyl)-2 H -1,2,3-triazole-4,5-diyl)-bis(1,2,4-oxadiazole) was synthesized from a readily accessible bis-cyano-substituted-azole in three steps with good yield.