高能量密度材料3,3′-偶氮-1,2,4,5-四嗪衍生物的分子设计

doi:10.3866/PKU.WHXB20101211

物理化学学报 >> 2010, Vol. 26 >> Issue (12): 3337-3344.doi: 10.3866/PKU.WHXB20101211

高能量密度材料3,3′-偶氮-1,2,4,5-四嗪衍生物的分子设计

张婧婧¹, 高洪伟², 卫涛², 王朝杰²

1. 温州医学院仁济学院, 浙江温州325035;
2. 温州医学院药学院, 浙江温州325035

收稿日期:2010-07-19 修回日期:2010-09-19 发布日期:2010-12-01
通讯作者: 卫涛 E-mail:weitao@wzmc.edu.cn
基金资助:
浙江省自然科学基金(Y5080043)资助项目

Molecular Design of 3,3′-Azobis-1,2,4,5-tetrazine-Based High-Energy Density Materials

ZHANG Jing-Jing¹, GAO Hong-Wei², WEI Tao², WANG Chao-Jie²

1. Renji College, Wenzhou Medical College, Wenzhou 325035, Zhejiang Province, P. R. China;
2. Department of Pharmacy, Wenzhou Medical College, Wenzhou 325035, Zhejiang Province, P. R. China

Received:2010-07-19 Revised:2010-09-19 Published:2010-12-01
Contact: WEI Tao E-mail:weitao@wzmc.edu.cn
Supported by:
The project was supported by the Natural Science Foundation of Zhejiang Province, China (Y5080043).

摘要/Abstract

摘要：

运用密度泛函理论(DFT)方法, 计算系列3,3′-偶氮-1,2,4,5-四嗪衍生物的生成热. 结果显示: —N3取代基在增加3,3′-偶氮-1,2,4,5-四嗪衍生物的生成热方面起了非常重要的作用. 通过分析标题化合物的最弱键离解能发现: —NH2或—N3取代基非常有利于增加衍生物的热稳定性. 计算的爆速(D)和爆压(p)数值表明: —NO2 或—NF2取代基有利于提高3,3′-偶氮-1,2,4,5-四嗪衍生物的爆轰性能. 综合爆轰性能和热稳定性的计算结果, 3 种3,3′-偶氮-1,2,4,5-四嗪衍生物可以作为潜在的品优高能量密度材料(HEDM)候选物.

关键词: 密度泛函理论, 3,3′-偶氮-1,2,4,5-四嗪, 生成热, 键离解能, 爆轰性能

Abstract:

We systematically studied the heats of formation (HOFs) for a series of 3,3′-azobis-1,2,4, 5-tetrazine derivatives by density functional theory (DFT). The results show that the —N3 group plays a very important role in increasing the HOFs for these derivatives. An analysis of the bond dissociation energies for the weakest bonds indicates that the attachment of —NH2 or —N3 group to 3,3′-azobis-1,2,4, 5-tetrazine is favorable in enhancing its thermal stability. The calculated detonation velocities (D) and pressures (p) indicates that —NO2 or —NF2 largely enhances the detonation performance of the derivatives. Considering the detonation performance and the thermal stability, the three derivatives may be regarded to be promising candidates for high-energy density materials (HEDMs).

Key words: Density functional theory, 3,3′-Azobis-1,2,4,5-tetrazine, Heat of formation, Bond dissociation energy, Detonation property

MSC2000:

O641

张婧婧, 高洪伟, 卫涛, 王朝杰. 高能量密度材料3,3′-偶氮-1,2,4,5-四嗪衍生物的分子设计[J]. 物理化学学报, 2010, 26(12): 3337-3344.

ZHANG Jing-Jing, GAO Hong-Wei, WEI Tao, WANG Chao-Jie. Molecular Design of 3,3′-Azobis-1,2,4,5-tetrazine-Based High-Energy Density Materials[J]. Acta Phys. -Chim. Sin., 2010, 26(12): 3337-3344.

参考文献

1. Huynh, M. H. V.; Hiskey, M. A.; Pollard, C. J.; Montoya, D. P.; Hartline, E. L.; Gilardi, R. D. J. Energ. Mater., 2004, 22: 217
2. Huynh, M. H. V.; Hiskey, M. A.; Archuleta, J. G.; Roemer, E. L.; Gilardi, R. D. Angew. Chem. Int. Edit., 2004, 43: 5658
3. Talawar, M. B.; Sivabalan, R.; Senthilkumar, N.; Prabhu, G.; Asthana, S. N. J. Hazard. Mater., 2004, 113: 11
4. Wei, T.; Zhu,W. H.; Zhang, X.W.; Li, Y. F.; Xiao, H. M. J. Phys. Chem. A, 2009, 113: 9404
5. Wei, T.; Zhu,W. H.; Zhang, J. J.; Xiao, H. M. J. Hazard. Mater., 2010, 179: 581
6. Chavez, D. E.; Hiskey, M. A.; Gilardi, R. D. Org. Lett., 2004, 6: 2889
7. Chavez, D. E.; Hiskey, M. A. J. Energ. Mater., 1999, 17: 357
8. Wilcox, C. F.; Zhang, Y. X.; Bauer, S. H. J. Energ. Mater., 2002, 20: 71
9. Chavez, D. E.; Hiskey, M. A.; Gilardi, R. D. Angew. Chem. Int. Edit., 2000, 39: 1791
10. Kerth, J.; L?bbecke, S. Propellants Explos. Pyrotech., 2002, 27: 111
11. L?bbecke, S.; Schuppler, H.; Schweikert,W. J. Therm. Anal. Calorim., 2003, 72: 453
12. Chavez, D. E.; Hiskey, M. A.; Naud, D. L. Propellants Explos. Pyrotech., 2004, 29: 209
13. Rice, B. M.; Hare, J. Thermochim. Acta, 2002, 384: 377
14. Muthurajan, H.; Sivabalan, R.; Talawar, M. B.; Anniyappan, M.; Venugopalan, S. J. Hazard. Mater., 2006, 133: 30
15. Hohenberg, P.; Kohn,W. Phys. Rev. B, 1964, 136: 864
16. Kohn,W.; Sham, L. J. Phys. Rev. A, 1965, 140: 1133
17. Salahub D. R.; Zerner, M. C. The challenge of d and f electrons. Washington D.C.: ACS, 1989
18. Parr, R. G.; Yang,W. Density-functional theory of atoms and molecules. Oxford: Oxford University Press, 1989: 1-333
19. Chen, Z. X.; Xiao, J. M.; Xiao, H. M.; Chiu, Y. N. J. Phys. Chem. A, 1999, 103: 8062
20. Xiao, H. M.; Chen, Z. X. The modern theory for tetrazole chemistry. Beijing: Science Press, 2000: 128-158
[肖鹤鸣, 陈兆旭. 四唑化学的现代理论. 北京: 科学出版社, 2000: 128-158]
21. Chen, P. C.; Chieh, Y. C.; Tzeng, S. C. J. Mol. Struct. -Theochem, 2003, 634: 215
22. Ju, X. H.; Li, Y. M.; Xiao, H. M. J. Phys. Chem. A, 2005, 109: 934
23. Hahre,W. J.; Radom, L.; Schleyer, P. V. R.; Pole, J. A. Ab initio molecular orbital theory. New York:Wiley-Interscience, 1986
24. Wang, F.; Xu, X. J.; Xiao, H. M.; Zhang, J. Acta Chim. Sin., 2003, 61: 1939
[王飞, 许晓娟, 肖鹤鸣, 张骥. 化学学报, 2003, 61: 1939]
25. Ju, X. H.;Wang, X.; Bei, F. L. J. Comput. Chem., 2005, 26: 1263
26. (a) David, R. L. Handbook of chemistry and physics. 84th ed. CRC Press, 2003-2004: sect 5 (b) Afeefy, H. Y.; Liebman, J. F.; Stein, S. E.“Neutral thermochemical data”in NIST chemistry webbook, NIST standard reference database number 69. Eds. Linstrom, P. J.; Mallard, W. G. Gaithersburg, MD: National Institute of Standards and Technology, 2000 (http://webbook.nist.gov) (c) Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard,W. G. J. Phys. Chem. Ref. Data, 1988: Suppl. No.1
27. Curtiss, L. A.; Raghavachari, K.; Trucks, G.W.; Pople, J. A. J. Chem. Phys., 1991, 94: 7221
28. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople, J. A. J. Chem. Phys., 1997, 106: 1063
29. Benson, S.W. Thermochemical kinetics. 2nd ed. New York: Wiley-Interscience, 1976
30. Mills, I.; Cvitas, T.; Homann, K.; Kallay, N.; Kuchitsu, K. Quantities, units, and symbols in physical chemistry. Oxford: Blackwell Scientific Publications, 1988: 1-233
31. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res., 2003, 36: 255
32. Kamlet, M. J.; Jacobs, S. J. J. Chem. Phys., 1968, 48: 23
33. Rice, B. M.; Hare, J. J.; Byrd, E. F. C. J. Phys. Chem. A, 2007, 111: 10874
34. Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 09. Revision A.01.Wallingford, CT: Gaussian Inc., 2009
35. Scott, A. P.; Radom, L. J. Phys. Chem., 1996, 100: 16502
36. Huynh, M. H. V.; Hiskey, M. A.; Chavez, D. E.; Naud, D. L.; Gilardi, R. D. J. Am. Chem. Soc., 2005, 127: 12537
37. Owens, F. J. J. Mol. Struct. -Theochem, 1996, 370: 11
38. Rice, B. M.; Sahu, S.; Owens, F. J. J. Mol. Struct. -Theochem, 1996, 583: 69
39. Talawar, M. B.; Sivabalan, R.; Mukundan, T.; Muthurajan, H.; Sikder, A. K.; Gandhe, B. R.; Subhananda, R. A. J. Hazard. Mater., 2009, 161: 589
40. Türker, L.; Atalar, T.; Gümüs, S.; ?amur, Y. J. Hazard. Mater., 2009, 167: 440
41. Smith, M.W.; Cliff, M. D. NTO-Based explosive formulations: a technology review. Australia: DSTO-TR-0796, 1999: 19-20
42. Gálvez-Ruiz, J. C.; Holl, G.; Karaghiosoff, K.; Klap?tke, T. M. L?hnwitz, K.; Mayer, P.; N?th, H.; Polborn, K.; Rohbogner, C. J.; Suter, M.;Weigand, J. J. Inorg. Chem., 2005, 44: 4237
43. Zhang, M. X.; Eaton, P. E.; Gilardi, R. D. Angew. Chem. Int. Edit., 2000, 39: 401

[1]	李诗涵,赵侦超,李世坤,邢友东,张维萍. DFT计算结合固体NMR研究富铝SSZ-13的铝分布和Brønsted酸性[J]. 物理化学学报, 2020, 36(4): 1903021 -0 .
[2]	黄智超,戴亚中,温晓杰,刘丹,林宇轩,徐珍,裴坚,吴凯. Au(111)表面Verdazyl自由基的构象转换[J]. 物理化学学报, 2020, 36(1): 1907043 -0 .
[3]	王丹,丁迅雷,廖珩璐,戴佳钰. 单个金或银原子掺杂的氧化钒团簇上的甲烷活化反应[J]. 物理化学学报, 2019, 35(9): 1005 -1013 .
[4]	陈强,姜利学,李海方,陈娇娇,赵艳霞,何圣贵. 钒硼双原子阳离子活化甲烷研究[J]. 物理化学学报, 2019, 35(9): 1014 -1020 .
[5]	韩萌茹,周亚男,周旋,储伟. 通过g-C₃N₄担载MNi₁₂ (Fe, Co, Cu, Zn)纳米团簇调节甲烷化[J]. 物理化学学报, 2019, 35(8): 850 -857 .
[6]	赵越,崔佳桐,胡继闯,马嘉璧. VO_1-4⁺阳离子与n-C_mH_2m+2 (m = 3, 5, 7)烷烃的反应性研究：氧含量和碳链长度的影响[J]. 物理化学学报, 2019, 35(5): 531 -538 .
[7]	许文武,高嶷. 巯基保护的中空金纳米球[J]. 物理化学学报, 2018, 34(7): 770 -775 .
[8]	卢天,陈沁雪. 通过价层电子密度分析展现分子电子结构[J]. 物理化学学报, 2018, 34(5): 503 -513 .
[9]	尹玥琪,蒋梦绪,刘春光. Keggin型多酸负载的单原子催化剂(M₁/POM, M = Ni, Pd, Pt, Cu, Ag, Au, POM = [PW₁₂O₄₀]^3-)活化氮气分子的密度泛函理论计算研究[J]. 物理化学学报, 2018, 34(3): 270 -277 .
[10]	尹凡华,谭凯. 符合独立五元环规则的C₁₀₀(417)Cl₂₈形成机理的密度泛函理论研究[J]. 物理化学学报, 2018, 34(3): 256 -262 .
[11]	钟爱国,李嵘嵘,洪琴,张杰,陈丹. 从能量和信息理论视角理解单取代烷烃的异构化[J]. 物理化学学报, 2018, 34(3): 303 -313 .
[12]	丁晓琴,丁俊杰,李大禹,潘里,裴承新. 基于概念密度泛函理论磷酸酯类反应性物质毒性预测[J]. 物理化学学报, 2018, 34(3): 314 -322 .
[13]	王心怡,谢磊,丁元琪,姚心仪,张弛,孔惠慧,王利坤,许维. 超高真空条件下碱基与金属在Au(111)表面的相互作用[J]. 物理化学学报, 2018, 34(12): 1321 -1333 .
[14]	陈驰,张雪,周志有,张新胜,孙世刚. S掺杂促进Fe/N/C催化剂氧还原活性的实验与理论研究[J]. 物理化学学报, 2017, 33(9): 1875 -1883 .
[15]	刘玉玉,李杰伟,薄一凡,杨磊,张效霏,解令海,仪明东,黄维. 芴基张力半导体结构和光电性质的理论研究[J]. 物理化学学报, 2017, 33(9): 1803 -1810 .

高能量密度材料3,3′-偶氮-1,2,4,5-四嗪衍生物的分子设计

Molecular Design of 3,3′-Azobis-1,2,4,5-tetrazine-Based High-Energy Density Materials

PDF (PC)

赞

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

Metrics

本文评价

推荐阅读 0