3,3’-偶氮-1,2,4-三唑含能衍生物的分子设计与性能预测
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摘要
运用密度泛函理论B3LYP方法,在6-31G~(**)水平上研究了3,3’-偶氮-1,2,4-三唑衍生物分子的几何结构、密度、生成焓、键离解能、爆轰参数、静电势、撞击感度以及产气性能。结果显示,-NHNO_2取代基在增加3,3’-偶氮-1,2,4-三唑衍生物的生成焓方面起着重要的作用。分析最弱键离解能发现,-NHNO_2取代基会降低衍生物热稳定性,而-NH_2和取代基会提高衍生物的热稳定性。计算衍生物爆速和爆压表明,-NO_2、-NHNO_2和-NF_2有利于提高衍生物的爆轰性能。根据计算结果,3种3,3’-偶氮-1,2,4-三唑衍生物可作为潜在的高能量密度含能材料候选物,其中1,1’,5,5’-四氨基-3,3’-偶氮基-1,2,4-三唑可作为新型高能产气药候选物。
The geometric configuration,density,enthalpy of formation,detonation properties,bond dissociation energy,electrostatic potential distribution,impact sensitivity and gas production performance of 3,3’-azobis-1,2,4-triazole derivatives were studied by density functional theory at DFT-B3LYP/6-31G~(**)level.The results show that the-NHNO_2group plays a very important role in increasing the HOF(Heat of Formation)for 3,3’-azobis-1,2,4-triazole derivatives,and an analysis of the weakest bond dissociation energy can find that the-NHNO_2 group can reduce the thermal stability of the derivatives,while the group of-NH_2 can increase the thermal stability of the derivatives.The calculated detonation velocity(D)and detonation pressure(p)of the derivatives indicate that-NO_2,-NHNO_2 and-NF_2are beneficial to improve the detonation performance.According to the calculation results,the three derivatives may be regarded to be promising candidates for high-energy density materials(HEDMs).,1,1’,5,5’-tetraamino-3,3’-azobis-1,2,4-triazole can be used as a candidate for new high-energy gas generating agent.
The geometric configuration,density,enthalpy of formation,detonation properties,bond dissociation energy,electrostatic potential distribution,impact sensitivity and gas production performance of 3,3’-azobis-1,2,4-triazole derivatives were studied by density functional theory at DFT-B3LYP/6-31G~(**)level.The results show that the-NHNO_2group plays a very important role in increasing the HOF(Heat of Formation)for 3,3’-azobis-1,2,4-triazole derivatives,and an analysis of the weakest bond dissociation energy can find that the-NHNO_2 group can reduce the thermal stability of the derivatives,while the group of-NH_2 can increase the thermal stability of the derivatives.The calculated detonation velocity(D)and detonation pressure(p)of the derivatives indicate that-NO_2,-NHNO_2 and-NF_2are beneficial to improve the detonation performance.According to the calculation results,the three derivatives may be regarded to be promising candidates for high-energy density materials(HEDMs).,1,1’,5,5’-tetraamino-3,3’-azobis-1,2,4-triazole can be used as a candidate for new high-energy gas generating agent.
引文
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[2]阳世清,岳守体.国外四嗪四唑类高氮含能材料研究进展[J].含能材料,2003,11(4):231-235.
[3]NAUD D L,HISKEY M A,HARRY H H.Synthesis and Explosive Properties of 5,5'-Dinitro-3,3'-azo-1 H-1,2,4-triazole(DNAT)[J].Journal of Energetic Materials,2003,21(1):56-62.
[4]WANG K,SHU Y,LIU N,et al.Theoretical studies on structure and performance of[1,2,5]-oxadiazolo-[3,4-d]-pyridazine-based derivatives[J].Journal of Physical Organic Chemistry,2017,30(1):2-9.
[5]黄辉,黄风雷,聂福德,等.钝感高能炸药研究进展[R]中国工程物理研究院科技年报.2013:3-8.
[6]李云路,刘田英,曹端林,等.四硝基吡咯及其衍生物结构与性能的理论研究[J].含能材料,2017,25(4):291-297.
[7]张婧婧,高洪伟,卫涛,等.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.
[8]BECKE A D.Density-functional thermochemistry.V.Systematic optimization of exchange-correlation functionals[J].Journal of Chemical Physics,1997,107(20):8554-8560.
[9]LU T,CHEN F.Multiwfn:a multifunctional wavefunction analyzer.[J].Journal of Computational Chemistry,2012,33(5):580-592.
[10]林梦海.量子化学计算方法与应用[M].北京:科学出版社,2004.
[11]RICE B M,BYRD E F C.Evaluation of electrostatic descriptors for predicting crystalline density[J].Journal of Computational Chemistry,2013,34(25):2146-2151.
[12]HEHRE W J.Ab initio molecular orbital theory[M]Ab initio molecular orbital theory.Wiley,1986:399-406.
[12]毕福强,王玉,王伯周,et al.多硝甲基氧化偶氮呋咱含能衍生物爆轰与安全性能理论研究[J].含能材料,2016,24(11):1063-1069.
[13]肖鹤鸣,许晓娟,邱玲.高能量密度材料的理论设计[M].北京:科学出版社,2008.
[14]POLITZER P,LANE P,MURRAY J S.Computational Characterization of a Potential Energetic Compound:1,3,5,7-Tetranitro-2,4,6,8-tetraazacubane[J].Central European Journal of Energetic Materials,2011,8(1):39-52.
[15]POLITZER P,MURRAY J S.Some Perspectives on Estimating Detonation Properties of C,H,N,O Compounds[J].Cent.Eur.J.Energ.Mater,2011,8(3):209-220.
[16]PETERPOLITZER,MURRAY J S,GRICE M E,et al.Calculation of heats of sublimation and solid phase heats of formation[J].Molecular Physics,1997,91(5):923-928.
[17]BYRD E F,RICE B M.Improved prediction of heats of formation of energetic materials using quantum mechanical calculations.[J].Journal of Physical Chemistry A,2006,110(3):1005-13.
[18]KAMLET M J,JACOBS S J.Chemistry of Detonations.I.ASimple Method for Calculating Detonation Properties of C-H-N-O Explosives[J].Journal of Chemical Physics,1968,48(1):23-35.
[19]KAMLET M J,HURWITZ H.Chemistry of Detonations.IV.Evaluation of a Simple Predictional Method for Detonation Velocities of C-H-N-O Explosives[J].Journal of Chemical Physics,1968,48(8):3685-3692.
[20]LI Yunlu,WU Junpeng,CAO Duanlin,et al.Theoretical Study on the Effects of Hydrogen-Bonding and MoleculeCation Interactions on the Sensitivity of HMX[J].Journal of Physical Chemistry A,2016,120(42):8444-8449.
[21]POSPIL,MIROSLAV,VáVRA,et al.A possible crystal volume factor in the impact sensitivities of some energetic compounds[J].Journal of Molecular Modeling,2010,16(5):895-901.
[22]WU Q,ZHU W,XIAO H.Quantum chemical studies on three novel 1,2,4-triazole,N-oxides as potential insensitive high explosives[J].Journal of Molecular Modeling,2014,20(9):2441.
[23]LU T,CHEN F W.Atomic Dipole Moment Corrected Hirshfeld Population Method[J].Journal of Theoretical&Computational Chemistry,2012,11,163-183.
[24]卢天,陈飞武.原子电荷计算方法的对比[J].物理化学学报2012,28(1):1-18.
[25]LU T,CHEN F W.Multiwfn:A Multifunctional Wavefunction Analyzer[J].J.Comput.Chem,2012,33,580-592.
[26]张婧婧,高洪伟,卫涛,等.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.