Citation: Bu-Tong LI, Lu-Lin LI, Ju PENG. Theoretical Exploration about the Detonation Performance and Thermal Stability of the Nitro-substituted Derivatives of Guanine[J]. Chinese Journal of Structural Chemistry, ;2021, 40(4): 409-414. doi: 10.14102/j.cnki.0254-5861.2011-2954 shu

Theoretical Exploration about the Detonation Performance and Thermal Stability of the Nitro-substituted Derivatives of Guanine

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

Corresponding author: Bu-Tong LI, libutong@hotmail.com Lu-Lin LI, lulin.li@outlook.com
Received Date: 5 August 2020
Accepted Date: 28 September 2020

Fund Project: the Natural Science Foundation of Guizhou Province QKHPTRC[2018]5778-09the Natural Science Foundation of Guizhou Province QKHJC[2020] 1Y038the Natural Science Foundation of Guizhou Education University 14BS017the Natural Science Foundation of Guizhou Education University 2019ZD001

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The nitro-substituted derivatives of guanine are designed and calculated to explore novel high energy density materials. To explore the thermal stability of title molecules, the heat of formation (HOF), bond dissociation energy (BDE), and bond order of the trigger bond are calculated. To predict the possibility used as high energy density compounds, the detonation pressure (P), detonation velocity (D), explosive heat (Q), and crystal density (ρ) are calculated by using the classical Kamlet-Jacobs (K-J) equation. Based on our calculations, E (D = 8.93 km/s, P = 37.21 GPa) is confirmed as the potential high energy density compound.
- high energy density compounds,
- Kamlet-Jacobs equation,
- density function theory,
- guanine derivatives
1. [1]
  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
2. [2]
  Carvalho, T. M. T.; Amaral, L. M. P. F.; Morais, V. M. F.; Ribeiro da Silva, M. D. M. C. Calorimetric and computational studies for three nitroimidazole isomers. J. Chem. Thermodyn. 2017, 105, 267−275. doi: 10.1016/j.jct.2016.10.026
3. [3]
  Ravi, P. Experimental study and ab-initio calculations on the molecular structure, infrared and raman spectral properties of dinitroimidazoles. Chem. Data Collect. 2017, 9−10, 11−23.
4. [4]
  Eberly, J. O.; Mayo, M. L.; Carr, M. R.; Crocker, F. H.; Indest, K. J. Detection of hexahydro-1,3-5-trinitro-1,3,5-triazine (RDX) with a microbial sensor. J. Gen. Appl. Microbiol. 2019, 64, 139−144.
5. [5]
  Ariyarathna, T.; Ballentine, M.; Vlahos, P.; Smith, R. W.; Cooper, C.; Bohlke, J. K.; Fallis, S.; Groshens, T. J.; Tobias, C. Tracing the cycling and fate of the munition, hexahydro-1,3,5-trinitro-1,3,5-triazine in a simulated sandy coastal marine habitat with a stable isotopic tracer, (15)N-[RDX]. Sci. Total Environ. 2019, 647, 369−378. doi: 10.1016/j.scitotenv.2018.07.404
6. [6]
  Wu, J.; Huang, Y.; Yang, L.; Geng, D.; Wang, F.; Wang, H.; Chen, L. Reactive molecular dynamics simulations of the thermal decomposition mechanism of 1,3,3-trinitroazetidine (TNAZ). ChemPhysChem. 2018, 2683−2695.
7. [7]
  Li, Y.; Feng, X.; Liu, H.; Hao, J.; Redfern, S. A. T.; Lei, W.; Liu, D.; Ma, Y. Route to high-energy density polymeric nitrogen t-N via He-N compounds. Nat. Commun. 2018, 9, 722−728. doi: 10.1038/s41467-018-03200-4
8. [8]
  Vetter, I. R.; Wittinghofer, A. The guanine nucleotide-binding switch in three dimensions. Science 2001, 294, 1299−1304. doi: 10.1126/science.1062023
9. [9]
  Li, B.; Li, L. Theoretical study on nitroimine derivatives of azetidine as high-energy-density compounds. Cent. Eur. J. Energetic Mater. 2020, 17, 107−118. doi: 10.22211/cejem/119139
10. [10]
  Li, B.; Li, L.; Luo, T. Theoretical exploration about the thermal stability and detonation properties of nitro-substituted hypoxanthine. J. Mol. Model. 2020, 26, 114, 23−28.
11. [11]
  Ravi, P.; Tewari, S. P. A dft study on the structure-property relationship of amino-, nitro-and nitrosotetrazoles, and their n-oxides: new high energy density molecules. Struct. Chem. 2012, 23, 487−498. doi: 10.1007/s11224-011-9898-5
12. [12]
  Zheng, Y. Dbl family guanine nucleotide exchange factors. Trends Biochem. Sci. 2001, 26, 724−732. doi: 10.1016/S0968-0004(01)01973-9
13. [13]
  Henderson, E.; Hardin, C. C.; Walk, S. K.; Tinoco Jr, I.; Blackburn, E. H. Telomeric DNA oligonucleotides form novel intramolecular structures containing guanine· guanine base pairs. Cell 1987, 51, 899−908. doi: 10.1016/0092-8674(87)90577-0
14. [14]
  Yu, H. Dft study on reaction mechanism of proton transfer of guanine. J. Wuhan Univ. (Nat. Sci. Ed.) 2012, 58, 35−39.
15. [15]
  Lee, C.; Yang, W.; Parr, R. G. Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37, 785−789. doi: 10.1103/PhysRevB.37.785
16. [16]
  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 03, Revision B. 01, Gaussian, Inc., Pittsburgh PA 2003.
17. [17]
  Ghule, V. D.; Jadhav, P. M.; Patil, R. S.; Radhakrishnan, S.; Soman, T. Quantum-chemical studies on hexaazaisowurtzitanes. J. Phys. Chem. A 2009, 114, 498−503.
18. [18]
  Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. Molecular orbital theory of the electronic structure of organic compounds. V. Molecular theory of bond separation. J. Am. Chem. Soc. 1970, 92, 4796−4801. doi: 10.1021/ja00719a006
19. [19]
  Fan, X. W.; Ju, X. H. Theoretical studies on four-membered ring compounds with NF₂, ONO₂, N₃, and NO₂ groups. J. Comput. Chem. 2008, 29, 505−513. doi: 10.1002/jcc.20809
20. [20]
  Rice, B. M.; Pai, S. V.; Hare, J. Predicting heats of formation of energetic materials using quantum mechanical calculations. Combust. Flame 1999, 118, 445−458. doi: 10.1016/S0010-2180(99)00008-5
21. [21]
  Linstrom, P. J.; Mallard, W. G. The nist chemistry webbook: a chemical data resource on the internet. J. Chem. Eng. Data 2001, 46, 1059−1063. doi: 10.1021/je000236i
22. [22]
  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
23. [23]
  Paquet, L.; Monteil-Rivera, F.; Hatzinger, P. B.; Fuller, M. E.; Hawari, J. Analysis of the key intermediates of rdx (hexahydro-1,3,5-trinitro-1,3,5-triazine) in groundwater: occurrence, stability and preservation. J. Environ. Monit. 2011, 13, 2304−2311. doi: 10.1039/c1em10329f
24. [24]
  Emel'yanenko, V. N.; Zaitsau, D. H.; Verevkin, S. P. Thermochemical properties of xanthine and hypoxanthine revisited. J. Chem. Eng. Data 2017, 62, 2606−2609. doi: 10.1021/acs.jced.7b00085
25. [25]
  Li, B.; Li, L.; Ye, M. Thermal stability and detonation character of nitro-substituted derivatives of cytosine. Chem. Phys. 2020, 536, 110846−5. doi: 10.1016/j.chemphys.2020.110846
26. [26]
  Drake, R. High-Energy-Density Physics: Fundamentals, Inertial Fusion, and Experimental Astrophysics (Shock Wave and High Pressure Phenomena). Springer, Berlin 2006, p214−215
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