Theoretical studies on oxadiazole-based layer stacking nitrogen-rich high-performance insensitive energetic materials
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ORIGINAL PAPER
Theoretical studies on oxadiazole-based layer stacking nitrogen-rich high-performance insensitive energetic materials Yan Huang 1 & Qian Zhang 1 & Le-Wu Zhan 1 & Jing Hou 1
&
Bin-Dong Li 1
Received: 9 July 2020 / Accepted: 17 September 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract A series of energetic compounds derived from substituted oxadiazole molecules which were theoretically proved to have π–π stacking crystal structure using NIC method and QTAIM theory were designed and investigated theoretically as novel highperformance insensitive energetic materials. The heats of formation (HOFs) and detonation parameters were predicted based on Kamlet–Jacobs equations and Born–Haber cycle. All energetic compounds and derivatives were calculated at DFT-B3PW91/631G++(d,p) level and exhibited ideal oxygen balance (OB%) (− 19.50~15.68), positive heats of formation (424.0~957.4 kJ/mol), and pleasant crystal density (1.707~1.901 g/cm3). The predicted results revealed that detonation performances of some designed molecules are equal to traditional energetic materials while they are more stable and insensitive that can be considered to have potential synthesis and application value. Keywords Heterocycles . Intermolecular interaction . Layer stacking structure . Oxadiazole . HIEMs
Introduction During the past decade, great efforts have been focused on the development of high-performance insensitive energetic materials (HIEMs) [1–3]. Layer-by-layer stacking structure induced by intermolecular interactions, such as van der Waals forces, hydrogen bonding, and π–π stacking, has been discovered in the crystal structures of some HIEMs and found to affect physicochemical and detonation properties [4, 5]. For Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00894-020-04555-6) contains supplementary material, which is available to authorized users. * Jing Hou [email protected] * Bin-Dong Li [email protected] Yan Huang [email protected] Qian Zhang [email protected] Le-Wu Zhan [email protected] 1
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
instance, some traditional HIEMs such as TATB (2,4,6triamino-1,3,5-trinitro-benzene), DAAzF (3,3′-diamino-4,4′azofurazan), and FOX-7 (1,1-diamino-2,2-dinitroethene) were confirmed to have layered crystal packing with reasonable interlayer spacing [6]. In 2017, Shreeve and co-workers synthesized 1,2,9,10-tetranitro-dipyrazolo [1,5-d:5′,1′-f] [1,2,3,4] tetrazine which exhibits excellent performance and high thermal stability and demonstrated that the two pyrazole rings and 1,2,3,4-tetrazine ring of the compound are coplanar [7]. Therefore, designing and synthesizing new planar nitrogen-rich heterocycles represent an attractive approach to obtain potential high-performance insensitive energetic materials. Rakitin group synthesized bis[1,2,5]oxadiazolo[3,4c:3′,4′-]pyridazine 4,5-dioxide that could be regarded as tautomer of 4,4′-dinitroso-3,3′-bifuraz
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