Synthesis
DOI: 10.1055/a-2262-9396
paper

Synthesis of (5-Iminio-4,5-dihydro-1,3,4-oxadiazol-2-yl)tetrazol-1-ide: A Zwitterionic Compound Containing a Tetrazole Anion as a Promising Blunt Energetic Material

Yaxin Liu
,
Meifang Lv
,
Guofeng Zhang
,
Zhiwen Ye


Abstract

(5-Iminio-4,5-dihydro-1,3,4-oxadiazol-2-yl)tetrazol-1-ide is the first zwitterionic energetic material containing tetrazole as an anion and 1,3,4 oxadiazole as a cation. Its low mechanical sensitivity (IS >40 J, FS >360 N) and high gas volume after detonation at standard temperature and pressure (767.0 dm3/kg) make it a prime example of a novel type of blunt energetic material with promising applications.

Supporting Information



Publikationsverlauf

Eingereicht: 20. November 2023

Angenommen nach Revision: 06. Februar 2024

Accepted Manuscript online:
06. Februar 2024

Artikel online veröffentlicht:
21. Februar 2024

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  • References

  • 1 Francois EG, Chavez DE, Sandstrom MN. Propellants, Explos., Pyrotech. 2010; 35: 529
  • 2 Solodyuk GD, Boldyrev MD, Gidaspov BV, Nikolaev VD. Zh. Org. Khim. 1981; 17: 861
  • 3 Fischer N, Fischer D, Klapötke TM, Piercey DG, Stierstorfer J. J. Mater. Chem. 2012; 22: 20418
  • 4 Göbel M, Karaghiosoff K, Klapötke TM, Piercey DG, Stierstorfer J. J. Am. Chem. Soc. 2010; 132: 17216
  • 5 Licht H. Propellants, Explos., Pyrotech. 2000; 25: 126
  • 6 Tarchoun AF, Trache D, Klapötke TM, Khimeche K. Chem. Eng. J. 2020; 400: 125960
  • 7 Wurzenberger MH. H, Endrass SM. J, Lommel M, Klapötke TM, Stierstorfer J. ACS Appl. Energy Mater. 2020; 3: 3798
  • 8 Reichel M, Wurzenberger MH. H, Lommel M, Kofen M, Krumm B, Stierstorfer J, Karaghiosoff K. Z. Anorg. Allg. Chem. 2021; 647: 347
  • 9 Swain PK, Singh H, Tewari SP. J. Mol. Liq. 2010; 151: 87
  • 10 Du Y, Qu ZK, Wang HC, Cui H, Wang XJ. Propellants, Explos., Pyrotech. 2021; 46: 860
  • 11 Politzer P, Concha MC, Grice ME, Murray JS, Lane P. J. Mol. Struct.: THEOCHEM 1998; 452: 75
  • 12 Churakov AM, Tartakovsky VA. Chem. Rev. 2004; 104: 2601
  • 13 Türker L, Variş S. Polycyclic Aromat. Compd. 2009; 29: 228
  • 14 Wozniak DR, Zeller M, Byrd E, Piercey D. RSC Adv. 2021; 11: 17710
  • 15 Gu H, Xiong H, Yang H, Cheng G. Chem. Eng. J. 2021; 408: 128021
  • 16 Ma Q, Zhang G, Li J, Liao L, Huang J, Fan G, Nie F. ChemistrySelect 2018; 3: 1650
  • 17 Yount J, Zeller M, Byrd EF. C, Piercey DG. Inorg. Chem. 2021; 60: 16204
  • 18 Klapötke TM, Krumm B, Pfluger C. J. Org. Chem. 2016; 81: 6123
  • 19 Fischer D, Gottfried JL, Klapötke TM, Karaghiosoff K, Stierstorfer J, Witkowski D. Angew. Chem. Int. Ed. 2016; 55: 16132
  • 20 Sun G, Chen H, Esseghir M, Fan R, Wang SE. Chemical Foaming Agents Containing Tosyl Groups. US 0265077A1, 2021
  • 21 Lu T, Chen F. J. Comput. Chem. 2012; 33: 580
  • 22 Lu T, Chen F. J. Mol. Graphics Modell. 2012; 38: 314
  • 23 Humphrey W, Dalke A, Schulten K. J. Mol. Graphics 1996; 14: 33
  • 24 Zhang J, Lu T. Phys. Chem. Chem. Phys. 2021; 23: 20323
  • 25 Johnson ER, Keinan S, Mori-Sánchez P, Contreras-García J, Cohen AJ, Yang W. J. Am. Chem. Soc. 2010; 132: 6498
  • 26 Turner MJ, McKinnon JJ, Wolff SK, Grimwood DJ, Spackman PR, Jayatilaka D, Spackman MA. CrystalExplorer17 . University of Western Australia; Australia: 2017
  • 27 Spackman PR, Turner MJ, McKinnon JJ, Wolff SK, Grimwood DJ, Jayatilakab D, Spackman MA. J. Appl. Crystallogr. 2021; 54: 1006
  • 28 Lu T, Manzetti S. Struct. Chem. 2014; 25: 1521
  • 29 Zhang JH, Shreeve JM. J. Phys. Chem. C 2015; 119: 12887
  • 30 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision A.1 Gaussian, Inc.: Wallingford CT, 2009 .
  • 31 Súceska M. EXPLO5 (Revision 6.01) . Brodarski Institute; Croatia: 2013