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Issue 20, 2020
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Energetic N-azidomethyl derivatives of polynitro hexaazaisowurtzitanes series: CL-20 analogues having the highest enthalpy

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Abstract

High endothermicity is one of the most important factors in the design of high-performance energetic materials for a new generation of rocket technologies. Taking this into account, in this study, novel highly energetic cage compounds were synthesized by the incorporation of a high-enthalpy N-azidomethyl moiety into the polynitro hexaazaisowurtzitane backbone. All obtained compounds were fully characterized by high-resolution mass spectrometry, IR and multinuclear NMR (1H, 13C, 14N, 15N) spectroscopy. For two of them, 4-azidomethyl-2,6,8,10,12-pentanitrohexaazaisowurtzitane and 4,10-bis(azidomethyl)-2,6,8,12-tetranitrohexaazaisowurtzitane, the density and structural features were established by X-ray diffractometry. Enthalpies of formation were determined experimentally by combustion calorimetry. Thermal stability measurements and testing of impact and friction sensitivity were also carried out. The synthesized compounds exhibit a high level of heat resistance (decomposition onset 180–205 °C) and density (1.85–1.93 g cm−3). Their enthalpies of formation on a unit of mass (up to 2210 kJ kg−1) are the highest among the known hexaazaisowurtzitane derivatives and are 2–2.5 times that of CL-20. The combination of these attractive properties makes the new materials promising energetic components for propellant compositions.

Graphical abstract: Energetic N-azidomethyl derivatives of polynitro hexaazaisowurtzitanes series: CL-20 analogues having the highest enthalpy

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Article information


Submitted
24 Mar 2020
Accepted
22 Apr 2020
First published
23 Apr 2020

New J. Chem., 2020,44, 8357-8365
Article type
Paper

Energetic N-azidomethyl derivatives of polynitro hexaazaisowurtzitanes series: CL-20 analogues having the highest enthalpy

O. A. Luk′yanov, V. V. Parakhin, N. I. Shlykova, A. O. Dmitrienko, E. K. Melnikova, T. S. Kon'kova, K. A. Monogarov and D. B. Meerov, New J. Chem., 2020, 44, 8357
DOI: 10.1039/D0NJ01453B

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