Статья
2020
Effect of Substituents on the Energy Barrier of Internal Rotation in Aminonitroethylenes
B. E. Krisyuk, T. M. Sypko
Российский журнал прикладной химии
https://doi.org/10.1134/S1070427220060178
Abstract / Full Text
Promising energetic materials 1,1-diamino-2,2-dinitroethylene (DADNE) and its derivatives in which one or both hydrogen atoms of the amino group are substituted by the NH2 or OH group were studied by quantum-chemical methods using PBE0 hybrid functional with the cc-pVDZ basis set and the coupled cluster method on the CCSD/aug-cc-pVDZ level. The thermal stability of such substances depends on the energy barrier of internal rotation Er around the C=C bond. The above-indicated substituents decrease Er . The value of Er is mainly determined by the structure of intramolecular hydrogen bonds. Introduction of the amino group leads to a more pronounced decrease in Er than introduction of the hydroxy group does.
Author information
- Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, 142432, Moscow oblast, RussiaB. E. Krisyuk & T. M. Sypko
- Moscow State University, 119991, Moscow, RussiaT. M. Sypko
References
- Latypov, N.V., Bergman, J., Langlet, A., Wellmar, U., and Bemm, U., Tetrahedron, 1998, vol. 54, no. 38, pp. 11525–11536. https://doi.org/10.1016/S0040-4020(98)00673-5
- Bellamy, A.J., Structure and Bonding, Mingos, D.M.P., Ed., Berlin: Springer, 2007, vol. 125, pp. 1–33. https://doi.org/10.1007/430_2006_054
- Sikder, A.K. and Sikder, N., J. Hazard. Mater., 2004, vol. 112, nos. 1–2, pp. 1–15. https://doi.org/10.1016/j.jhazmat.2004.04.003
- Trzciński, W.A., Cudziło, S., Chyłek, Z., and Szymańczyk, L., J. Hazard. Mater., 2008, vol. 157, nos. 2–3, pp. 605–612. https://doi.org/10.1016/j.jhazmat.2008.01.026
- Nair, U.R., Asthana, S.N., Subhananda Rao, A., and Gandhe, B.R., Defence Sci. J., 2010, vol. 60, no. 2, pp. 137–151. https://doi.org/10.14429/dsj.60.327
- Liu, Y., Li, F., and Sun, H., Theor. Chem. Acc., 2014, vol. 133, no. 10, ID 1557. https://doi.org/10.1007/s00214-014-1567-5
- Jiang, H., Jiao, Q., and Zhang, C., J. Phys. Chem. C, 2018, vol. 122, no. 27, pp. 15125–15132. https://doi.org/10.1021/acs.jpcc.8b03691
- Burnham, A.K., Weese, R.K., Wang, R., Kwok, Q.S.M., and Jones, D.E.G., Thermal properties of FOX-7, 35th Int. Annual Conf. of ICT, Karlsruhe (Germany), 2005, publ. 70.
- Gindulyte, A., Massa, L., Huang, L., and Karle, J., J. Phys. Chem. A, 1999, vol. 103, no. 50, pp. 11045–11051. https://doi.org/10.1021/jp991794a
- Khrapkovskii, G.M., Nikolaeva, E.V., Chachkov, D.V., and Shamov, A.G., Russ. J. Gen. Chem., 2004, vol. 74, no. 6, pp. 908–920. https://doi.org/10.1023/B:RUGC.0000042427.28020.77
- Kiselev, V.G. and Gritsan, N.P., J. Phys. Chem. A, 2014, vol. 118, no. 36, pp. 8002–8008. https://doi.org/10.1021/jp507102x
- Krisyuk, B.E. and Veretin, V.S., Butlerovsk. Soobshch., 2017, vol. 49, no. 2, pp. 31–35.
- Krisyuk, B.E., Russ. J. Phys. Chem. B, 2020, vol. 14, no. 1, pp. 1–4. https://doi.org/10.1134/S1990793120010054
- Bellamy, A.J., Latypov, N.V., and Goede, P., J. Chem. Res. (S), 2002, no. 7, pp. 257–257. https://doi.org/10.3184/030823402103172103
- Axthammer, Q.J., Krumm, B., and Klapötke, T.M., J. Phys. Chem. A, 2017, vol. 121, no. 18, pp. 3567–3579. https://doi.org/10.1021/acs.jpca.7b01742
- Katritzky, A.R., Sommen, G.L., Gromova, A.V., Witek, R.M., Steel, P.J., and Damavarapu, R., Chem. Heterocyclic Compd., 2005, vol. 41, no. 1, pp. 127–134.
- Frumkin, A.E., Yudin, N.V., Suponitsky, K.Yu., and Sheremetev, A.B., Mendeleev Commun., 2018, vol. 28, no. 2, pp. 135–137. https://doi.org/10.1016/j.mencom.2018.03.007
- Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision C.01, Wallingford, CT: Gaussian, 2009.
- Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., and Montgomery, J.A., J. Comput. Chem., 1993, vol. 14, no. 11, pp. 1347–1363. https://doi.org/10.1002/jcc.540141112
- Adamo, C. and Barone, V., J. Chem. Phys., 1999, vol. 110, no. 13, pp. 6158–6170. https://doi.org/10.1063/1.478522