All possible isomers of N-unsubstituted 3,5-di(nitropyrazolyl)-1,2,4-oxadiazoles were synthesized. The influence of regioisomerism was studied with respect to density, thermal stability, impact and friction sensitivity, and energetic performance.
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(а) Zlotin, S. G.; Dalinger, I. L.; Makhova, N. N.; Tartakovsky, V. A. Russ. Chem. Rev. 2020, 89, 1. (b) Zlotin, S. G.; Churakov, A. M.; Egorov, M. P.; Fershtat, L. L.; Klenov, M. S.; Kuchurov, I. V.; Makhova, N. N.; Smirnov, G. A.; Tomilov, Y. V.; Tartakovsky, V. A. Mendeleev Commun. 2021, 31, 731.
(a) Pepekin, V. I. Russ. J. Phys. Chem. B 2010, 4, 954. (b) Pepekin, V. I. Russ. J. Phys. Chem. B 2011, 5, 41. (c) Dalinger, I. L.; Suponitsky, K. Yu.; Pivkina, A. N.; Sheremetev, A. B. Propellants, Explos., Pyrotech. 2016, 41, 789. (d) Zhou, J.; Zhang, J. L.; Wang, B. Z.; Qiu, L. L.; Xu, R. Q.; Sheremetev, A. B. FirePhysChem 2021. https://doi.org/10.1016/j.fpc.2021.09.005
(a) Manelis, G. B.; Nazin, G. M.; Rubtsov, Z. I.; Strunin, V. A. Termicheskoe razlozhenie i gorenie vzryvchatykh vechshestv i porokhov (Thermal decomposition and burning of explosives and powders [in Russian]); Nauka: Moscow, 1995. (b) Sikder, A. K.; Sikder, N. J. Hazardous Mat. 2004, 112, 1.
(a) Pagoria, P. Propellants, Explos., Pyrotech. 2016, 41, 452. (b) Klapotke, T. M.; Witkowski, T. G. Propellants, Explos., Pyrotech. 2016, 41, 470. (c) Tang, Y.; He, C.; Imler, G. H.; Parrish, D. A.; Shreeve, J. M. Chem. Commun. 2018, 54, 10566.
Wang, Q.; Wang, S.; Feng, X.; Wu, L.; Zhang, G.; Zhou, M.; Wang, B.; Yang, L. ACS Appl. Mater. Interfaces 2017, 9, 37542.
Huo, X.; Wang, F.; Niu, L. L.; Gou, R.; Zhang, C. FirePhysChem 2021, 1, 8.
Li, H.; Zhang, L.; Petrutik, N.; Wang, K.; Ma, Q.; Shem-Tov, D.; Zhao, F.; Gozin, M. ACS Cent. Sci. 2020, 6, 54.
(a) He, C.; Yin, P.; Mitchell, L. A.; Parrish, D. A.; Shreeve, J. M. Chem. Commun. 2016, 52, 8123. (b) Koch, E.-C. Def. Technol. 2019, 15, 467.
(a) Zhang, M.; Fu, W.; Li, C.; Gao, H.; Tang, L.; Zhou, Z. Eur. J. Inorg. Chem. 2017, 2883. (b) Gutowski, L.; Cudzilo, S. Def. Technol. 2021, 17, 775.
Chen, D.; Xiong, H.; Yang, H.; Tang, J.; Cheng, G. FirePhysChem 2021, 1, 71.
(a) Dalinger, I. L.; Vatsadze, I. A.; Shkineva, T. K.; Kormanov, A. V.; Struchkova, M. I.; Suponitsky, K. Yu.; Bragin, A. A.; Monogarov, K. A.; Sinditskii, V. P.; Sheremetev, A. B. Chem.–Asian J. 2015, 10, 1987. (b) Lempert, D. B.; Dalinger, I. L.; Shu, Y.-J.; Kazakov, A. I.; Sheremetev, A. B. Chin. J. Explos. Propellants 2016, 39, 16. (c) Sinditskii, V. P.; Hoang, T. H.; Smirnova, A. D.; Egorshev, V. Yu.; Yudin, N. V.; Vatsadze, I. A.; Dalinger, I. L. Thermochim. Acta 2018, 667, 1. (d) Dalinger, I. L.; Kormanov, A. V.; Suponitsky, K. Yu.; Muravyev, N. V.; Sheremetev, A. B. Chem.–Asian J. 2018, 13, 1165. (e) Lempert, D. B.; Kazakov, A. I.; Soglasnova, S. I.; Dalinger, I. L.; Sheremetev, A. B. Russ. Chem. Bull. 2018, 67, 1580. (f) Kazakov, A. I.; Kurochkina, L. S.; Nabatova, A. V.; Lempert, D. B.; Dalinger, I. L.; Kormanov, A. V.; Serushkina, O. V.; Sheremetev, A. B. Dokl. Phys. Chem. 2018, 478, 15. (g) Yan, T.; Yang, H.; Yang, C.; Yi, Z.; Zhua, S.; Cheng, G. J. Mat. Chem. A 2020, 8, 23857.
(a) Tang, Y.; He, C.; Imler, G. H.; Parrish, D. A.; Shreeve, J. M. Chem. Commun. 2018, 54, 10566. (b) Yan, T.; Cheng, G.; Yang, H. New J. Chem. 2020, 44, 6643.
(a) Shevelev, S. A.; Dalinger, I. L.; Shkineva, T. K.; Ugrak, B. I.; Gulevskaya, V. I.; Kanishchev, M. I. Russ. Chem. Bull. 1993, 42, 1063. (b) Dalinger, I. L.; Zubanova, N. I.; Kuzmin, V. S.; Shevelev, S. A. Russ. Chem. Bull. 1993, 42, 1211.
(a) Fu, Z.; Wang, Y.; Yang, L.; Su, R.; Chen, J.; Nie, F.; Huang, J.; Chen, F.-X. RSC Adv. 2014, 4, 11859. (b) Wang, Z.; Zhang, H.; Jabeen, F.; Gopinathan-Pillai, G.; Arami, J. A.; Killian, B. J.; Stiegler, K. D.; Yudewitz, D. S.; Thiemann, P. L.; Turk, J. D.; Zhou, W.; Steel, P. J.; Hall, C. D.; Katritzky, A. R. Eur. J. Org. Chem. 2015, 7468. (c) Chavez, D. E.; Schulze, M. C.; Parrish, D. A. Chem. Heterocycl. Compd. 2017, 53, 737. (d) Pagoria, P. F.; Zhang, M.-X.; Zuckerman, N. B. Chem. Heterocycl. Compd. 2017, 53, 760. (e) Hermann, T. S.; Klapötke, T. M.; Krumm, B.; Stierstorfer, J. Asian J. Org. Chem. 2018, 7, 739. (f) Johnson, E. C.; Sabatini, J. J.; Chavez, D. E.; Sausa, R. C.; Byrd, E. F. C.; Wingard, L. A.; Guzman, P. E. Org. Process Res. Dev. 2018, 22, 736. (g) Bennion, J. C.; Batyrev, I. G.; Ciezak-Jenkins, J. A. Propellants, Explos., Pyrotech. 2019, 44, 160. (h) Xue, Q.; Bi, F.; Zhang, J.; Wang, Z.; Zhai, L.; Huo, H.; Wang, B.; Zhang, S. Front. Chem. 2020, 7, 942.
(a) Xiong, H.; Cheng, G.; Zhang, Z.; Yang, H. New J. Chem. 2019, 43, 7784. (b) Tang, Y.; Gao, H.; Mitchell, L. A.; Parrish, D. A.; Shreeve, J. M. Angew. Chem., Int. Ed. 2016, 55, 3200. (c) Qu, Y.; Zeng, Q.; Wang, J.; Ma, Q.; Li, H.; Li, H.; Yang, H. Chem.–Eur. J. 2016, 22, 12527. (d) Li, B.; Luo, Y.; Wang, H.; Ju, R.; Lei, W.; Zhang, M. Propellants, Explos., Pyrotech. 2020, 45, 1870.
(a) Dalinger, I. L.; Shkineva, T. K.; Vatsadze, I. A.; Kormanov, A. V.; Kozeev, A. M.; Suponitsky, K. Yu.; Pivkina, A. N.; Sheremetev, A. B. FirePhysChem 2021, 1, 83. (b) Sinditskii, V. P.; Smirnova, A. D.; Serushkin, V. V.; Yudin, N. V.; Vatsadze, I. A.; Dalinger, I. L.; Kiselev, V. G.; Sheremetev, A. B. Thermochim. Acta 2021, 698, 178876. (c) Kormanov, A. V.; Lipilin, D. L.; Shkineva, T. K.; Vatsadze, I. A.; Kozeev, A. M.; Dalinger, I. L. Chem. Heterocycl. Compd. 2017, 53, 876. (d) Dalinger, I. L.; Vatsadze, I. A.; Shkineva, T. K.; Kormanov, A. V.; Kozeev, A. M.; Sheremetev, A. B.; Averkiev, B. B.; Dalinger, A. I.; Beklemishev, M. K. Chem. Heterocycl. Compd. 2015, 51, 545.
Yan, T.; Cheng, G.; Yang, H. ChemPlusChem 2019, 84, 1567.
Shkineva, T. K.; Vatsadze, I. A.; Khoranyan, T. E.; Lipilin, D. L.; Pivkina, A. N.; Dalinger, I. L. Chem. Heterocycl. Compd. 2021, 57, 828.
(a) Baykov, S.; Sharonova, T.; Osipyan, A.; Rozhkov, S.; Shetnev, A.; Smirnov, A. Tetrahedron Lett. 2016, 57, 2898. (b) Baykov, S.; Sharonova, T.; Shetnev, A.; Rozhkov, S.; Kalinin S.; Smirnov, A. Tetrahedron 2017, 73, 945.
(a) Kayukova, L. A. Pharm. Chem. J. 2005, 39, 539. (b) Pace, A.; Buscemi, S.; Piccionello, A. P.; Pibiri, I. Adv. Heterocycl. Chem. 2015, 116, 85.
Dosa, S.; Daniels, J.; Gütschow, M. J. Heterocycl. Chem. 2011, 48, 407.
Outirite, M.; Lebrini, M.; Lagrenee, M.; Bentiss, F. J. Heterocycl. Chem. 2007, 44, 1529.
Vatsadze, I. A.; Serushkina, O. V.; Dutov, M. D.; Shkineva, T. K.; Suponitsky, K. Yu.; Ugrak, B. I.; Dalinger, I. L. Chem. Heterocycl. Compd. 2015, 51, 695.
Zaitsev A. A.; Dalinger, I. L.; Shevelev, S. A. Russ. Chem. Rev. 2009, 78, 589.
(a) Benson, S. W.; Cruickshank, F. R.; Golden, D. M.; Haugen, G. R.; O'Neal, H. E.; Rodgers, A. S.; Shaw, R.; Walsh, R. Chem. Rev. 1969, 69, 279. (b) Lebedev, Yu. A.; Miroshnichenko, E. A.; Knobel, Yu. K. Termokhimiya nitrosoedinenii (Thermochemistry of nitro compounds [in Russian]); Nauka: Moscow, 1970, p. 168. (c) Kustova, L. V.; Kirpichev, E. P.; Pubtsov, Y. I.; Avdonin, V. V.; Korepin, A. G.; Eremenko, L. T. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1981, 30, 1830. (d) Holmes, J. L.; Aubry, C. J. Phys. Chem. A 2012, 116, 7196.
Bu, R.; Xiong, Y.; Wei, X.; Li, H.; Zhang, C. Cryst. Growth Des. 2019, 19, 5981.
Pepekin, V. I.; Lebedev, Yu. A. Dokl. Akad. Nauk USSR 1977, 234, 1391.
Muravyev, N. V.; Meerov, D. B.; Monogarov, K. A.; Melnikov, I. N.; Kosareva, E. K.; Fershtat, L. L.; Sheremetev, A. B.; Dalinger, I. L.; Fomenkov, I. V.; Pivkina, A. N. Chem. Eng. J. 2021, 421, 129804.
Muravyev, N. V.; Monogarov, K. A.; Bragin, A. A.; Fomenkov, I. V.; Pivkina, A. N. Thermochim. Acta 2016, 631, 1.
Lei, C.; Yang, H.; Cheng, G. Dalton Trans. 2020, 49, 1660.
(a) Černovská, K.; Kemter, M.; Gallmeier, H. C.; Rzepecki, P.; Schrader, T.; König, B. Org. Biomol. Chem. 2004, 2, 1603. (b) Semeraro, T.; Mugnaini, C.; Manetti, F.; Pasquini, S.; Corelli, F. Tetrahedron 2008, 64, 11249.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(1), 37–44
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Khoranyan, T.E., Shkineva, T.K., Vatsadze, I.A. et al. Regioisomeric 3,5-di(nitropyrazolyl)-1,2,4-oxadiazoles and their energetic properties. Chem Heterocycl Comp 58, 37–44 (2022). https://doi.org/10.1007/s10593-022-03054-1
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DOI: https://doi.org/10.1007/s10593-022-03054-1