Citation: Bu-Tong LI, Lu-Lin LI, Jia-Xin HE. Looking for High Energy Density Molecules in the Nitro-substituted Derivatives of Pyridazine[J]. Chinese Journal of Structural Chemistry, ;2020, 39(5): 849-854. doi: 10.14102/j.cnki.0254–5861.2011–2531 shu

Looking for High Energy Density Molecules in the Nitro-substituted Derivatives of Pyridazine

School of Chemistry and Materials Science, Guizhou Education University, Guiyang 550018, China

Corresponding author: Bu-Tong LI, libutong@hotmail.com
Received Date: 15 July 2019
Accepted Date: 18 September 2019

Fund Project: the Foundation of Natural Science of Guizhou Education University 14BS017

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A series of derivatives of pyridazine were designed through substituting hydrogens on the pyridazine ring with nitro groups. To explore the thermal stability of the title molecules, heats of formation, bond dissociation energies, and bond orders were calculated at the B3PW91/6-311+G(d, p) level. To confirm the potential usage as high energy density compounds, the detonation pressure and detonation velocity were predicted by using the empirical Kamlet-Jacobs (K-J) equation. Based on our calculated results, both thermal and kinetic stabilities of the title molecules are confirmed with good detonation characters. Especially, 3, 4, 5-trinitropyridazide and 3, 4, 6-trinitropyridazide represent excellent detonation parameters better than 1, 3, 5-trinitro-1, 3, 5-triazacyclohexane (RDX) and are screened out as potential high energy density compounds.
- quantum chemistry,
- high energy density compounds,
- density functional theory,
- Kamlet-Jacobs equation
1. [1]
  Boddu, V. M.; Viswanath, D. S.; Ghosh, T. K.; Damavarapu, R. 2, 4, 6-Triamino-1, 3, 5-trinitrobenzene (TATB) and TATB-based formulations — a review. J. Hazard. Mater. 2010, 181, 1–8. doi: 10.1016/j.jhazmat.2010.04.120
2. [2]
  Ariyarathna, T.; Vlahos, P.; Tobias, C.; Smith, R. Sorption kinetics of TNT and RDX in anaerobic freshwater and marine sediments: batch studies. Environ. Toxicol. Chem. 2016, 35, 47–55. doi: 10.1002/etc.3149
3. [3]
  Wang, X.; Wang, Y.; Miao, M.; Zhong, X.; Lv, J.; Cui, T.; Li, J.; Chen, L.; Pickard, C. J.; Ma, Y. Cagelike diamondoid nitrogen at high pressures. Phys. Rev. Lett. 2012, 109, 175502–175506. doi: 10.1103/PhysRevLett.109.175502
4. [4]
  Li, B.; Zhou, M.; Peng, J.; Li, L.; Guo, Y. Theoretical calculations about nitro-substituted pyridine as high-energy-density compounds (HEDCs). J. Mol. Model. 2019, 25, 23–28. doi: 10.1007/s00894-018-3904-4
5. [5]
  Liu, T.; Jia, J.; Li, B.; Gao, K. Theoretical exploration on structural stabilities and detonation properties of nitrimino substituted derivatives of cyclopropane. Chin. J. Struct. Chem. 2019, 38, 688–694.
6. [6]
  Gümüş, S. A computational study on substituted diazabenzenes. Turk. J. Chem. 2011, 35, 803–808.
7. [7]
  Gökçınar, E.; Klapötke, T. M.; Bellamy, A. J. Computational study on 2, 6-diamino-3, 5-dinitropyrazine and its 1-oxide and 1, 4-dioxide derivatives. J. Mol. Struct. Theochem. 2010, 953, 18–23. doi: 10.1016/j.theochem.2010.04.015
8. [8]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh PA. Gaussian 03, Revision B. 01 2003.
9. [9]
  Kamlet, M. J.; Jacobs, S. J. Chemistry of detonations. I. A simple method for calculating detonation properties of C–H–N–O explosives. J. Chem. Phys. 1968, 48, 23–35. doi: 10.1063/1.1667908
10. [10]
  Glendening, E. D.; Landis, C. R.; Weinhold F. NBO 6.0: natural bond orbital analysis program. J. Comput. Chem. 2013, 34, 1429–1437. doi: 10.1002/jcc.23266
11. [11]
  Rice, B. M.; Sahu, S.; Owens, F. J. Density functional calculations of bond dissociation energies for NO₂ scission in some nitroaromatic molecules. J. Mol. Struct. Theochem. 2002, 583, 69–72. doi: 10.1016/S0166-1280(01)00782-5
12. [12]
  Harris, N. J.; Lammertsma, K. Ab initio density functional computations of conformations and bond dissociation energies for hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine. J. Am. Chem. Soc. 1997, 119, 6583–6589. doi: 10.1021/ja970392i
13. [13]
  Li, B.; Li, L.; Chen, S. Thermal stability and detonation character of nitro-substituted derivatives of imidazole. J. Mol. Model. 2019, 25, 298–304. doi: 10.1007/s00894-019-4190-5
14. [14]
  Ghule, V. D.; Sarangapani, R.; Jadhav, P. M.; Tewari, S. P. Theoretical studies on nitrogen rich energetic azoles. J. Mol. Model. 2011, 17, 1507–1515. doi: 10.1007/s00894-010-0848-8
15. [15]
  Jensen, T. L.; Moxnes, J. F.; Kjønstad, E. F.; Unneberg, E. A study of the detonation properties, propellant impulses, impact sensitivities and synthesis of nitrated anta and nto derivatives. Cent. Eur. J. Energetic Mater. 2016, 13, 445–467. doi: 10.22211/cejem/64995
16. [16]
  Sieranski, T. Discovering the stacking landscape of a pyridine-pyridine system. J. Mol. Model. 2017, 23, 338–353. doi: 10.1007/s00894-017-3496-4
17. [17]
  Pospíšil, M.; Vávra, P.; Concha, M.; Murray, J.; Politzer, P. A possible crystal volume factor in the impact sensitivities of some energetic compounds. J. Mol. Model. 2010, 16, 895–901. doi: 10.1007/s00894-009-0587-x
18. [18]
  Politzer, P.; Martinez, J.; Murray, J. S.; Concha, M. C.; Toro-Labbé, A. An electrostatic interaction correction for improved crystal density prediction. Mol. Phys. 2009, 107, 2095–2101. doi: 10.1080/00268970903156306
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