Computer-aided design and property prediction of novel insensitive high-energy heterocycle-substituted derivatives of ca
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ORIGINAL PAPER
Computer-aided design and property prediction of novel insensitive high-energy heterocycle-substituted derivatives of cage NNNAHP Raza Ullah Khan 1
&
Weihua Zhu 1
Received: 30 April 2020 / Accepted: 9 August 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract A series of new derivatives of cage 2,4,6,8,10,12,13,14,15-nanonitro-2,4,6,8,10,12,13,14, 15-nanoazaheptacyclo[5.5.1.13,11,15,9] pentadecane (NNNAHP) were designed by incorporating combination of heterocyclic and non-heterocyclic substituents and studied by using density functional theory. The results indicate that the –tetrazine and –N(NO2)2 are very beneficial structural fragments to increase their heat of formation. The introduction of different heterocyclic and non-heterocyclic groups can produce different effects on different properties: large densities (1.88–2.06 g cm−3), high detonation velocities (8.17–9.83 km s−1), excellent detonation pressures (30.55–46.02GPa), and outstanding heat of detonations (1169.80–1637.19 cal g−1). The analysis of bond dissociation energy values show that the N(cage)-NO2 is the weakest bond, and it may turn into a trigger bond during detonation. Almost all the derivatives are thermally more stable than the parent compound. All the substituted derivatives are insensitive as compared with the parent compound. According to excellent detonation properties, high thermal stability, and good insensitivity, 10 compounds may be chosen as potential high-energy density compounds. Keywords Density functional theory . Energetic properties . Heterocyclic substituents . Impact sensitivity . Thermal stability
Introduction Energetic compounds that store a huge amount of energy and can be handled safely (meaning they have high safety performance) are mainly developed by cut and try method that needs complex synthetic procedures coupled with standard characterization tests [1–5]. Such endeavors are time-intensive, manpower-exhaustive, and comparatively expensive, and moreover, the target candidates are not necessarily satisfied in the end. In fact, many energetic materials were developed over the years, but most of them are not applied in practice or even to be characterized since they have very high sensitivity [6]. The deficiency of the structure-property relationship of the
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00894-020-04513-2) contains supplementary material, which is available to authorized users. * Weihua Zhu [email protected] 1
Institute for Computation in Molecular and Materials Science, Department of Chemistry, Nanjing University of Science and Technology, Nanjing 210094, China
energetic compounds retards the development of new energetic materials. During the past couple of decades, researchers have diverted their attention from conventional nitro aromatic (TATB and TNT), nitro ester (PETN), and nitramine (RDX and HMX)-based energetic compounds whose energy mainly derives from the carbon framework’s oxidation to nitrated cage ske
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