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Novel energetic aminofurazans with a nitro-NNO-azoxy group

Nikita E Leonov 1
Nikita E Leonov
, 
Sergei Evgenievich Semenov 1, 2
Sergei Evgenievich Semenov
,  , 
Aleksandr Mikhailovich Churakov 1
Aleksandr Mikhailovich Churakov
, 
Yurii Andreevich Strelenko 1
Yurii Andreevich Strelenko
, 
Alevtina Nikolaevna Pivkina 3
Alevtina Nikolaevna Pivkina
, 
Ivan Vladimirovich Fedyanin 4, 5
Ivan Vladimirovich Fedyanin
,  , 
Tatiana Sergeevna Kon'kova 3
Tatiana Sergeevna Kon'kova
, 
Yurii Nikolaevich Matyushin 3
Yurii Nikolaevich Matyushin
, 
Evgeny Aleksandrovich Miroshnichenko 3
Evgeny Aleksandrovich Miroshnichenko
, 
Vladimir Alexandrovich Tartakovsky 1
Vladimir Alexandrovich Tartakovsky
10.1016/j.mencom.2021.11.006
Published 2021-11-08
Communication , Volume 31, Issue 6, 789-791
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Leonov N. E. et al. Novel energetic aminofurazans with a nitro-NNO-azoxy group // Mendeleev Communications. 2021. Vol. 31. No. 6. pp. 789-791.
GOST all authors (up to 50) Copy
Leonov N. E., Semenov S. E., Klenov M. S., Churakov A. M., Strelenko Y. A., Pivkina A. N., Fedyanin I. V., Lempert D. B., Kon'kova T. S., Matyushin Y. N., Miroshnichenko E. A., Tartakovsky V. A. Novel energetic aminofurazans with a nitro-NNO-azoxy group // Mendeleev Communications. 2021. Vol. 31. No. 6. pp. 789-791.
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TY - JOUR
DO - 10.1016/j.mencom.2021.11.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.11.006
TI - Novel energetic aminofurazans with a nitro-NNO-azoxy group
T2 - Mendeleev Communications
AU - Leonov, Nikita E
AU - Semenov, Sergei Evgenievich
AU - Klenov, Michael Sergeevich
AU - Churakov, Aleksandr Mikhailovich
AU - Strelenko, Yurii Andreevich
AU - Pivkina, Alevtina Nikolaevna
AU - Fedyanin, Ivan Vladimirovich
AU - Lempert, David Borisovich
AU - Kon'kova, Tatiana Sergeevna
AU - Matyushin, Yurii Nikolaevich
AU - Miroshnichenko, Evgeny Aleksandrovich
AU - Tartakovsky, Vladimir Alexandrovich
PY - 2021
DA - 2021/11/08
PB - Mendeleev Communications
SP - 789-791
IS - 6
VL - 31
ER -
BibTex
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@article{2021_Leonov,
author = {Nikita E Leonov and Sergei Evgenievich Semenov and Michael Sergeevich Klenov and Aleksandr Mikhailovich Churakov and Yurii Andreevich Strelenko and Alevtina Nikolaevna Pivkina and Ivan Vladimirovich Fedyanin and David Borisovich Lempert and Tatiana Sergeevna Kon'kova and Yurii Nikolaevich Matyushin and Evgeny Aleksandrovich Miroshnichenko and Vladimir Alexandrovich Tartakovsky},
title = {Novel energetic aminofurazans with a nitro-NNO-azoxy group},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.11.006},
number = {6},
pages = {789--791},
doi = {10.1016/j.mencom.2021.11.006}
}
MLA
Cite this
MLA Copy
Leonov, Nikita E., et al. “Novel energetic aminofurazans with a nitro-NNO-azoxy group.” Mendeleev Communications, vol. 31, no. 6, Nov. 2021, pp. 789-791. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.11.006.

Keywords

azoxy compounds
combustion calorimetry
differential scanning calorimetry
enthalpy of formation
furazans
nucleophilic substitution
X-ray diffraction analysis

Abstract

Novel energetic azoxy- and azofurazans bearing nitro-NNO- azoxy and amino groups were synthesized using the ammonolysis of some known (nitro-NNO-azoxy)furazans. 3-Amino-4-{[4′-(nitro-NNO-azoxy)f urazan-3′-yl]-NNO- azoxy}furazan displays the highest melting point (114 °C, decomp.) among the known (nitro-NNO-azoxy)furazans, optimal density (1.80 g cm−3), high experimental enthalpy of formation (639 kcal kg−1) and mechanical sensitivity on the level of PETN. In terms of the specific impulse level, the model solid composite propellant formulations based on this compound outperform similar formulations based on RDX, HMX or CL-20 by 7–12 s.

References

1.
10.1016/j.mencom.2021.11.006_b0005
Lempert
Cent. Eur. J. Energ. Mater., 2011
2.
10.1016/j.mencom.2021.11.006_b0010
Lempert
Chin. J. Explos. Propellants, 2015
3.
10.1016/j.mencom.2021.11.006_b0015
Klapötke
Chemistry of High-Energy Materials, 2017
5.
Fused heterocycle-based energetic materials (2012–2019)
Gao H., Zhang Q., Shreeve J.M.
Journal of Materials Chemistry A, 2020
6.
Energetic Heterocyclic N-Oxides
Chavez D.E.
Topics in Heterocyclic Chemistry, 2017
7.
10.1016/j.mencom.2021.11.006_b0035
Agrawal
Organic Chemistry of Explosives, 2007
8.
Synthesis and X-Ray Crystal Structure of Bis-3,3′-(nitro-NNO-azoxy)-difurazanyl Ether
Sheremetev A.B., Semenov S.E., Kuzmin V.S., Strelenko Y.A., Ioffe S.L.
Chemistry - A European Journal, 1998
9.
A comparative study of the structure, energetic performance and stability of nitro-NNO-azoxy substituted explosives
Wang Y., Li S., Li Y., Zhang R., Wang D., Pang S.
Journal of Materials Chemistry A, 2014
10.
Synthesis and Crystal Structure of Bis-3,3'-(nitro-NNO-azoxy)-4,4'-azofurazan
Li H., Wang B.Z., Li X.Z., Tong J.F., Lai W.P., Fan X.Z.
Bulletin of the Korean Chemical Society, 2013
11.
10.1016/j.mencom.2021.11.006_b0055
Li
Chin. J. Energ. Mater., 2014
12.
Design and theoretical study of 15 novel high energy density compounds
Lai W., Lian P., Liu Y., Yu T., Zhu W., Ge Z., Lv J.
Journal of Molecular Modeling, 2014
13.
10.1016/j.mencom.2021.11.006_b0065
Lian
Chin. J. Explos. Propellants, 2014
14.
Synthesis of New Energetic Materials Based on Furazan Rings and Nitro‐ NNO ‐azoxy Groups
Leonov N.E., Klenov M.S., Anikin O.V., Churakov A.M., Strelenko Y.A., Voronin A.A., Lempert D.B., Muravyev N.V., Fedyanin I.V., Semenov S.E., Tartakovsky V.A.
ChemistrySelect, 2020
15.
M. S. Klenov, N. E. Leonov, A. A. Guskov, A. M. Churakov, Yu. A. Strelenko and V. A. Tartakovsky, Russ. Chem. Bull., Int. Ed., 2019, 68, 1798 (Izv. Akad. Nauk, Ser. Khim., 2019, 1798).
16.
An Energetic (Nitro-NNO -azoxy)triazolo-1,2,4-triazine
Anikin O.V., Leonov N.E., Klenov M.S., Churakov A.M., Voronin A.A., Muravyev N.V., Strelenko Y.A., Fedyanin I.V., Tartakovsky V.A.
European Journal of Organic Chemistry, 2019
17.
First Synthesis of Aliphatic Nitro-NNO -azoxy Compounds
Leonov N.E., Klenov M.S., Anikin O.V., Churakov A.M., Strelenko Y.A., Monogarov K.A., Tartakovsky V.A.
European Journal of Organic Chemistry, 2018
18.
Churakov A.M., Ioffe S.L., Tartakovskii V.A.
Mendeleev Communications, 1996
19.
A new approach to synthesis of 1-aryl-2-nitrozodiazene 1-N-oxides
Churakov A.M., Semenov S.E., Ioffe S.L., Strelenko Y.A., Tartakovsky V.A.
Russian Chemical Bulletin, 1997
20.
10.1016/j.mencom.2021.11.006_b0100
High Energy Density Materials, 2007
21.
10.1016/j.mencom.2021.11.006_b0105
Zhilin
Malochuvstvitel’nye vzryvchatye veshchestva (Insensitive Explosives), 2008
22.
Nucleophilic substitution in the furazan series. Reactions of nitrofurazans with ammonia
Sheremetev A.B., Kulagina V.O., Kryazhevskikh I.A., Melnikova T.M., Aleksandrova N.S.
Russian Chemical Bulletin, 2002
23.
A. B. Sheremetev, O. V. Kharitonova, E. V. Mantseva, V. O. Kulagina, E. V. Shatunova, N. S. Aleksandrova, T. M. Mel’nikova, E. A. Ivanova, D. E. Dmitriev, V. A. Eman, I. L. Yudin, V. S. Kuz’min, Yu. A. Strelenko, T. S. Novikova, O. V. Lebedev and L. I. Khmel’nitskii, Russ. J. Org.Chem., 1999, 35, 1525 (Zh. Org. Khim., 1999, 35, 1555).
24.
NMR spectroscopic study of 3-nitrofurazans
Dmitriev D.E., Strelenko Y.A., Sheremetev A.B.
Russian Chemical Bulletin, 2013
25.
SHELXT– Integrated space-group and crystal-structure determination
Sheldrick G.M.
Acta Crystallographica Section A: Foundations and Advances, 2015
26.
Energetic N-azidomethyl derivatives of polynitro hexaazaisowurtzitanes series: CL-20 analogues having the highest enthalpy
Luk′yanov O.A., Parakhin V.V., Shlykova N.I., Dmitrienko A.O., Melnikova E.K., Kon'kova T.S., Monogarov K.A., Meerov D.B.
New Journal of Chemistry, 2020
27.
10.1016/j.mencom.2021.11.006_b0135
Sumin
Transactions of the 11th International Detonation Symposium, 1998
28.
10.1016/j.mencom.2021.11.006_b0140
Meyer
Explosives, 2016