Molecular design and property prediction of high density polynitro[3.3.3]-propellane-derivatized frameworks as potential high explosives

Journal of Physical Chemistry A

Volumn 118, Issue 45, 2014, Pages 10857-10865

  Zhang, Qinghua ^a   Zhang, Jiaheng ^b   Qi, Xiujuan ^a   Shreeve, Jean'ne M ^b  

^a RESEARCH CENTER OF LASER FUSION   (China)

^b UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY; DESIGN FOR TESTABILITY; EXPLOSIVES; MOLECULES; STRUCTURAL DESIGN;

DETONATION PROPERTIES; DETONATION VELOCITY; ENERGETIC MOLECULES; IMPACT SENSITIVITIES; INSENSITIVE HIGH EXPLOSIVE; PROPERTY PREDICTIONS; THERMODYNAMIC CALCULATIONS; TRICYCLIC STRUCTURE;

DETONATION;

EID: 84924310022     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp509549q     Document Type: Article

References (46)

1. Gao, H.; Shreeve, J. M. Azole-Based Energetic Salts. Chem. Rev. 2011, 111, 7377-7436.
2. Dippold, A. A.; Klapötke, T. M. A Study of Dinitro-bis-1, 2, 4-triazole-1, 1'-diol and Derivatives: Design of High-Performance Insensitive Energetic Materials by the Introduction of N-Oxides. J. Am. Chem. Soc. 2013, 135, 9931-9938.
3. Kettner, M. A.; Klapotke, T. M. 5, 5'-Bis-(trinitromethyl)-3, 3'-bi-(1, 2, 4-oxadiazole): A Stable Ternary CNO-Compound with High Density. Chem. Commun. 2014, 50, 2268-2270.
4. Fischer, N.; Fischer, D.; Klapotke, T. M.; Piercey, D. G.; Stierstorfer, J. Pushing the Limits of Energetic Materials-the Synthesis and Characterization of Dihydroxylammonium 5, 5'-Bistetrazole-1, 1'-diolate. J. Mater. Chem. 2012, 22, 20418-20422.
5. He, L.; Tao, G. H.; Parrish, D. A.; Shreeve, J. M. Impact Insensitive Dinitromethanide Salts. Chem. Commun. 2013, 49, 10329-10331.
6. Klapotke, T. M.; Petermayer, C.; Piercey, D. G.; Stierstorfer, J. 1, 3-Bis (nitroimido)-1, 2, 3-triazolate Anion, the N-Nitroimide Moiety, and the Strategy of Alternating Positive and Negative Charges in the Design of Energetic Materials. J. Am. Chem. Soc. 2012, 134, 20827-20836.
7. Zhang, J.; Shreeve, J. M. 3, 3'-Dinitroamino-4, 4'-azoxyfurazan and Its Derivatives: An Assembly of Diverse N-O Building Blocks for High-Performance Energetic Materials. J. Am. Chem. Soc. 2014, 136, 4437-4445.
8. Krause, H. H. In Energetic Materials; Teipel, U., Ed.; VCH: Weinheim, Germany, 2005; pp 1-25.
9. Klapotke, T. M. In High Energy Density Materials; Springer: Berlin, 2007; pp 85-121.
10. Klapotke, T. M. Chemistry of High-Energy Materials; Walter de Gruyter: Berlin, 2011.
11. Pagoria, P. F.; Lee, G. S.; Mitchell, A. R.; Schmidt, R. D. A Review of Energetic Materials Synthesis. Thermochim. Acta 2002, 384, 187-204.
12. Singh, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Energetic Nitrogen-Rich Salts and Ionic Liquids. Angew. Chem., Int. Ed. 2006, 45, 3584-3601.
13. Song, J.; Zhou, Z.; Dong, X.; Huang, H.; Cao, D.; Liang, L.; Wang, K.; Zhang, J.; Chen, F.; Wu, Y. Super-High-Energy Materials Based on Bis (2, 2-dinitroethyl) nitramine. J. Mater. Chem. 2012, 22, 3201-3209.
14. Lin, Q. H.; Li, Y. C; Qi, C; Liu, W.; Wang, Y.; S. Pang, P. Nitrogen-Rich Salts Based on 5-Hydrazino-1H-tetrazole: A New Family of High-Density Energetic Materials. J. Mater. Chem. A 2013, 1, 6776-6785.
15. Dong, H. The Development and Countermeasure of High Energy Density Materials. Chin. J. Energy Mater. 2004, 12, 1-12.
16. Liang, L.; Huang, H; Wang, K.; Bian, C; Song, J.; Ling, L.; Zhao, F.; Zhou, Z. Oxy-bridged Bis (1H-tetrazol-5-yl) furazan and Its Energetic Salts Paired with Nitrogen-Rich Cations: Highly Thermally Stable Energetic Materials with Low Sensitivity. J. Mater. Chem. 2012, 22, 21954-21964.
17. Yan, Q. L.; Zeman, S. Theoretical Evaluation of Sensitivity and Thermal Stability for High Explosives Based on Quantum Chemistry Methods: A Brief Review. Int. J. Quantum Chem. 2013, 113, 1049-1061.
18. Zhang, X.; Zhu, W.; Wei, T.; Zhang, C; Xiao, H. Densities, Heats of Formation, Energetic Properties, and Thermodynamics of Formation of Energetic Nitrogen-Rich Salts Containing Substituted Protonated and Methylated Tetrazole Cations: A Computational Study. J. Phys. Chem. C 2010, 114, 13142-13152.
19. Wang, F.; Du, H; Liu, H; Gong, X. Hydrogen-Bonding Interactions and Properties of Energetic Nitroamino[1, 3, 5]triazine-Based Guanidinium Salts: DFT-D and QTAIM Studies. Chem.-Asian J. 2012, 7, 2577-2591.
20. Gao, H; Ye, C.; Piekarski, C. M.; Shreeve, J. M. Computational Characterization of Energetic Salts. J. Phys. Chem. C 2007, 111, 10718-10731.
21. Zhu, W.; Yan, Q.; Li, J.; Cheng, B.; Shao, Y.; Xia, X.; Xiao, H. Prediction of the Properties and Thermodynamics of Formation for Energetic Nitrogen-Rich Salts Composed of Triaminoguanidinium Cation and 5-Nitroiminotetrazolate-Based Anions. J. Comput. Chem. 2012, 33, 1781-1789.
22. Taylor, D. E.; Rob, F.; Rice, B. M.; Podeszwa, R; Szalewicz, K A. Molecular Dynamics Study of 1, 1-Diamino-2, 2-dinitroethylene (FOX-7) Crystal Using A Symmetry Adapted Perturbation Theorybased Intermolecular Force Field. Phys. Chem. Chem. Phys. 2011, 13, 16629-16636.
23. Rice, B. M.; Hare, J. J. A Quantum Mechanical Investigation of the Relation between Impact Sensitivity and the Charge Distribution in Energetic Molecules. J. Phys. Chem. A 2002, 106, 1770-1783.
24. Gutowski, K. E.; Rogers, R D.; Dixon, D. A Accurate Thermochemical Properties for Energetic Materials Applications. II. Heats of Formation of Imidazolium-, 1, 2, 4-Triazolium-, and Tetrazolium-Based Energetic Salts from Isodesmic and Lattice Energy Calculations. J. Phys. Chem. B 2007, 111, 4788-4800.
25. Eaton, P. E.; Gilardi, R; Zhang, M. X. Polynitrocubanes: Advanced High-Density, High-Energy Materials. Adv. Mater. 2000, 12, 1143-1148.
26. Shin, M.; Kim, M. H; Ha, T.; Jeon, J.; Chung, K.; Kim, J. S.; Kim, Y. G. Synthesis of Novel 2, 4, 6, 8, 10-Pentaaza[3.3.3]propellane Derivatives. Tetrahedron 2014, 70, 1617-1620.
27. Shin, M.; Ha, T.; Chung, K.; Kim, J. S.; Kim, Y. G. Nitration of 3, 7, 9, 11-Tetraoxo-2, 4, 6, 8, 10-pentaaza[3.3.3]propellane. Appl. Chem. Eng. 2014, 25, 188-192.
28. Frisch, M. J.; Trucks, G W.; Schlegel, H. B.; Scuseria, G E.; Robb, M. A.; Cheeseman, J. R; Montgomery, J. A.; Jr., T. V; Kudin, K. N; Burant, J. C. et al. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
29. Bene, J. E. D.; Person, W. B.; Szczepaniak, K. Properties of Hydrogen-Bonded Complexes Obtained from the B3LYP Functional with 6-31G (d, p) and 6-31+G (d, p) Basis Sets: Comparison with MP2/6-31+G (d, p) Results and Experimental Data. J. Phys. Chem. 1995, 99, 10705-10707.
30. Wu, Q.; Zhu, W.; Xiao, H. Computer-aided Design of Two Novel and Super-High Energy Cage Explosives: Dodecanitrohexaprismane and Hexanitrohexaazaprismane. RSC Adv. 2014, 4, 3789-3797.
31. Wu, Q.; Zhu, W.; Xiao, H. A New Design Strategy for Highenergy Low-Sensitivity Explosives: Combining Oxygen Balance Equal to Zero, A Combination of Nitro and Amino Groups, and N-Oxide in One Molecule of 1-Amino-5-nitrotetrazole-3N-oxide. J. Mater. Chem. A 2014, 2, 13006-13015.
32. Wu, Q.; Pan, Y.; Zhu, W.; Xiao, H. Computational Study of Energetic Nitrogen-rich Derivatives of 1, 4-Bis (1-azo-2, 4-dinitrobenzene)-iminotetrazole. J. Mol. Model. 2013, 19, 1853-1864.
33. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. Assessment of Gaussian-2 and Density Functional Theories for the Computation of Enthalpies of Formation. J. Chem. Phys. 1997, 106, 1063-1079.
34. Atkins, P. W. Physical Chemistry; Oxford University Press: Oxford, U. K., 1982.
35. Politzer, P.; Murray, J. S.; Grice, M. E.; De Salvo, M.; Miller, E. Calculation of Heats of Sublimation and Solid Phase Heats of Formation. Mol. Phys. 1997, 91, 923-928.
36. Byrd, E. F. C.; Rice, B. M. Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Mechanical Calculations. J. Phys. Chem. A 2006, 110, 1005-1013.
37. Lu, T.; Chen, F. Multiwfn: A Multifunctional Wavefunction Analyzer. J. Comput. Chem. 2012, 33, 580-592.
38. 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.
39. Rice, B. M.; Byrd, E. F. C. Evaluation of Electrostatic Descriptors for Predicting Crystalline Density. J. Comput. Chem. 2013, 34, 2146-2151.
40. Sućeska, M. EXPLO5, version 6.01; Brodarski Institute: Zagreb, Croatia, 2013.
41. Gökçmar, E.; Klapötke, T. M.; Kramer, M. O. Computational Study on Nitronium and Nitrosonium Oxalate: Potential Oxidizers for Solid Rocket Propulsion? J. Phys. Chem. A 2010, 114, 8680-8686.
42. Pospíšil, M.; Vávra, P.; Concha, M. C.; Murray, J. S.; Politzer, P. A Possible Crystal Volume Factor in the Impact Sensitivities of Some Energetic Compounds. J. Mol. Model. 2010, 16, 895-901.
43. Zhu, W.; Zhang, C.; Wei, T.; Xiao, H. Computational Study of Energetic Nitrogen-rich Derivatives of 1, 1'- and 5, 5'-Bridged Ditetrazoles. J. Comput. Chem. 2011, 32, 2298-2312.
44. Vedachalam, M.; T. Ramakrishnan, V.; Boyer, J. H.; Dagley, I. J.; Nelson, K. A.; Adolph, H. G.; Gilardi, R.; George, C.; Flippen-Anderson, J. L. Facile Synthesis and Nitration of cis-Syn-cis-2, 6-dioxodecahydro-1H, 5H-diimidazo[4, 5-b:4', 5'-e]pyrazine. J. Org. Chem. 1991, 56, 3413-3419.
45. Dagley, I. J.; Flippen-Anderson, J. L. Synthesis of Cyclic Nitramines From Products of the Cyclocondensation Reaction of Guanidine With 2, 3, 5, 6-Tetrahydroxypiperazine-1, 4-dicarbaldehyde. Aust. J. Chem. 1994, 47, 2033-2045.
46. Guo, C.; Zhang, H.; Wang, X.; Liu, X.; Sun, J. Study on A Novel Energetic Cocrystal of TNT/TNB. J. Mater. Sci. 2013, 48, 1351-1357.