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Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives

Igor L'vovich Dalinger 1
Igor L'vovich Dalinger
, 
Alexander Khanonovich Shakhnes 1
Alexander Khanonovich Shakhnes
, 
Konstantin Alexandrovich Monogarov 2
Konstantin Alexandrovich Monogarov
, 
Kirill Yu Suponitsky 3
Kirill Yu Suponitsky
, 
Aleksei Borisovich Sheremetev 1
Aleksei Borisovich Sheremetev
10.1016/j.mencom.2015.11.010
Published 2015-11-09
Communication , Volume 25, Issue 6, 429-431
57
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Dalinger I. L. et al. Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 429-431.
GOST all authors (up to 50) Copy
Dalinger I. L., Shakhnes A. K., Monogarov K. A., Suponitsky K. Yu., Sheremetev A. B. Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 429-431.
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TY - JOUR
DO - 10.1016/j.mencom.2015.11.010
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.010
TI - Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives
T2 - Mendeleev Communications
AU - Dalinger, Igor L'vovich
AU - Shakhnes, Alexander Khanonovich
AU - Monogarov, Konstantin Alexandrovich
AU - Suponitsky, Kirill Yu
AU - Sheremetev, Aleksei Borisovich
PY - 2015
DA - 2015/11/09
PB - Mendeleev Communications
SP - 429-431
IS - 6
VL - 25
ER -
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@article{2015_Dalinger,
author = {Igor L'vovich Dalinger and Alexander Khanonovich Shakhnes and Konstantin Alexandrovich Monogarov and Kirill Yu Suponitsky and Aleksei Borisovich Sheremetev},
title = {Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.010},
number = {6},
pages = {429--431},
doi = {10.1016/j.mencom.2015.11.010}
}
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Dalinger, Igor L'vovich, et al. “Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives.” Mendeleev Communications, vol. 25, no. 6, Nov. 2015, pp. 429-431. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.010.

Abstract

Treatment of 1,1-dinitro-1-(3,5-dinitropyrazol-1-yl)methanide with electrophilic fluorinating or difluoroaminating agents affords the corresponding fluorodinitromethyl or (difluoroamino)dinitromethyl pyrazole derivatives. Single crystal X-ray diffraction analysis shows a remarkable high density and DSC exhibits acceptable thermal stability of the compounds.

References

1.
Organic fluorine compounds: a great opportunity for enhanced materials properties
Berger R., Resnati G., Metrangolo P., Weber E., Hulliger J.
Chemical Society Reviews, 2011
2.
(a) J. P. Agrawal and R. D. Hodgson, Organic Chemistry of Explosives, Wiley, Hoboken, 2007; (b) N. Kubota, Propellants and Explosives, Wiley-VCH, Weinheim, 2007; (c) M. N. Makhov and V. I. Arkhipov, Russ. J. Phys. Chem. B, 2008, 2, 602 (Khim. Fiz., 2008, 27, no. 8, 36); (d) D. Kumari, R. Balakshe, S. Banerjee and H. Singh, Rev. J. Chem., 2012, 2, 240.
3.
Chemistry of a-Halogenonitroalkanes
Fridman A.L., Surkov V.D., Novikov S.S.
Russian Chemical Reviews, 1980
4.
(a) G. K. Khisamutdinov,V. L. Korolev, I.Z. Kondyukov, I.S. Abdrakhmanov, S. P. Smirnov and A. A. Fainzilberg, Russ. Chem. Bull., 1993, 42, 1559 (Izv. Akad. Nauk, Ser. Khim., 1993, 1623); (b) I. V. Tselinskii, S.F. Mel’nikova, T.V. Romanova, S.V. Pirogov, G.K. Khisamutdinov, T.A. Mratkhuzina, V.L. Korolev, I.Z. Kondyukov, I.S. Abdrakhmanov and S. P. Smirnov, Russ. J. Org. Chem., 1997, 33, 1656 (Zh. Org. Khim., 1997, 33, 1739); (c) V. V. Semenov, M.I. Kanischev, S.A. Shevelev and A. S. Kiselyov, Tetrahedron, 2009, 65, 3441.
5.
(a) B. V. Litvinov, A.A. Fainzilberg, V.I. Pepekin, S.P. Smirnov, B.G. Loboiko, S.A. Shevelev, G.M. Nazin, Dokl. Akad. Nauk, 1994, 336, 67 (in Russian); (b) V. N. Grebennikov, G.M. Nazin and G. B. Manelis, Russ. Chem. Bull., 1995, 44, 628 (Izv. Akad. Nauk, Ser. Khim., 1995, 649); (c) V. N. Grebennikov, G.B. Manelis and G. M. Nazin, 27th International Annual Conference of ICT (Energetic Materials), 1996, 8.1-8.8; (d) A. V. Fokin, Yu. N. Studnev and L. D. Kuznetsova, Russ. Chem. Bull., 1996, 45, 1952 (Izv. Akad. Nauk, Ser. Khim., 1996, 2056); (e) V. Pepekin, Proceedings of the International Pyrotechnics Seminar, 1998, 24, 427; (f) G. M. Nazin, V.G. Prokudin and G. B. Manelis, Russ. Chem. Bull., Int. Ed., 2000, 49, 234.(Izv. Akad. Nauk, Ser. Khim., 2000, 231).
6.
R. D. Chapman, in High Energy Density Materials, ed. T. H. Klapotke, Structure and Bonding 125, ser. In: D. M. P. Mingos (Ed.), Springer-Verlag, Berlin, 2007, p. 123.
7.
Dalinger I.L., Shkineva T.K., Vatsadze I.A., Popova G.P., Shevelev S.A.
Mendeleev Communications, 2011
8.
Dalinger I.L., Vinogradov V.M., Shevelev S.A., Kuz’min V.S.
Mendeleev Communications, 1996
9.
10.1016/j.mencom.2015.11.010_bib0045
Fokin
Bull. Acad. Sci. USSR, Div. Chem. Sci, 1981
10.
(a) I. V. Tselinskii, A.A. Mel’nikov, L.G. Varyagina and A. E. Trubitsin, J. Org. Chem. USSR, 1985, 21, 2276 (Zh. Org. Khim., 1985, 21, 2490);(b) A. E. Trubitsin, A.A. Mel’nikov, I.V. Tselinskii and A. M. Popov, J. Org. Chem. USSR, 1990, 26, 1733 (Zh. Org. Khim., 1990, 26, 2007); (c) O. A. Luk’yanov, G.V. Pokhvisneva, T.V. Ternikova, N.I. Shlykova and M. E. Shagaeva, Russ. Chem. Bull., Int. Ed., 2011, 60, 1703.(Izv. Akad. Nauk, Ser. Khim., 2011, 1678).
11.
Synthesis and Crystal Structure of 2,3-Bis(dinitrofluoromethyl)-1,4-dioxane
Fedorov B.S., Golovina N.I., Smirnov S.P., Abdrakhmanov I.S., Firkin A.I., Atovmyan L.O.
Chemistry of Heterocyclic Compounds, 2002
13.
Polynitroethyl- and Fluorodinitroethyl Substituted Boron Esters
Klapötke T.M., Krumm B., Moll R.
Chemistry - A European Journal, 2013
14.
Mechanism of nitration of nitrogen-containing heterocyclic N-acetonyl derivatives. General approach to the synthesis of N-dinitromethylazoles
Semenov V.V., Shevelev S.A., Bruskin A.B., Kanishchev M.I., Baryshnikov A.T.
Russian Chemical Bulletin, 2009
15.
Novel Highly Energetic Pyrazoles:N-Trinitromethyl-Substituted Nitropyrazoles
Dalinger I.L., Vatsadze I.A., Shkineva T.K., Kormanov A.V., Struchkova M.I., Suponitsky K.Y., Bragin A.A., Monogarov K.A., Sinditskii V.P., Sheremetev A.B.
Chemistry - An Asian Journal, 2015
17.
(a) A. V. Fokin, Yu. N. Studnev and L. D. Kuznetsova, Dokl. Akad. Nauk, 1996, 346, 358 (in Russian); (b) A. V. Fokin, Yu. N. Studnev, A.I. Rapkin and L. D. Kuznetsova, Russ. Chem. Bull., 1996, 45, 2547.(Izv. Akad. Nauk, Ser. Khim., 1996, 2689).
18.
Sheremetev A.B., Yudin I.L., Suponitsky K.Y.
Mendeleev Communications, 2006
20.
Sheremetev A.B., Aleksandrova N.S., Suponitsky K.Y.
Mendeleev Communications, 2010
21.
(a) V. P. Lebedev, Y.N. Matyushin, Y.O. Inozemtcev, I.L. Dalinger, S. A. Shevelev and I. V. Fomenkov, 29th International Annual Conference of ICT (Energetic Materials), 1998, 180.1; (b) D. B. Lempert, G.N. Nechiporenko and S. I. Soglasnova, Khim. Fiz., 2005, 24, no. 3, 74.(in Russian).
22.
(a) S. W. Benson, F.R. Cruickshank, D.M. Golden, G.R. Haugen, H. E. O’Neal, A.S. Rodgers, R. Shaw and R. Walsh, Chem. Rev., 1969, 69, 279; (b) N. G. Zhitomirskaya and L. T. Eremenko, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1977, 26, 1595 (Izv. Akad. Nauk SSSR, Ser. Khim., 1977, 1822); (c) L. V. Kustova, E.P. Kirpichev, Yu. I. Pubtsov, V.V. Avdonin, A.G. Korepin and L. T. Eremenko, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1981, 30, 1813 (Izv. Akad. Nauk SSSR, Ser. Khim., 1981, 2232); (d) A. N. Kizin, P.L. Dvorkin, G.L. Ryzhova and Yu. A. Lebedev, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 343 (Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 372); (e) E. V. Sagadeev, A.A. Gimadeev and V. P. Barabanov, Theor. Found. Chem. Eng., 2009, 43, 108 (Teor. Osn. Khim. Tekhnol., 2009, 43, 114); (f) J. L. Holmes and C. Aubry, J. Phys. Chem. A 2012, 116, 7196.
23.
Equation of state for gases at high pressure
Kondrikov B.N., Sumin A.I.
Combustion, Explosion and Shock Waves, 1987