四嗪类高氮化合物结构与性能关系的理论研究
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摘要
本文的主要研究内容如下：
1．在总结分析大量文献的基础上对高氮化合物的组成单元进行了分类，主要分为结构单元、连接单元和取代基；对高氮化合物的实验和理论最新研究进展进行了综述，提出了以1，2，4，5-四嗪类化合物作为本论文的主要研究内容。
2．为了更清楚的了解结构单元之间的相互影响，设计了六元氮杂环和五元氮杂环取代1，2，4，5-四嗪得到了一系列化合物，采用量子化学计算方法对它们进行了详细的理论研究，讨论了各种氮杂环的改变对四嗪类化合物性能(包括生成热、密度以及爆速和爆压等)的影响，并找出爆轰性能较好的结构单元组合。
3．设计了连接桥(-N=N-)和取代基(-NH_2、-N_3)与1，2，4，5-四嗪环直接相连得到9种化合物，分析和讨论了它们的电子结构以及不同基团对生成热、爆速和爆压的贡献。
4．根据实验中已经合成且性能较好的高氮含能化合物BTATz和DAAT的结构特点和结构与性能关系的理论分析结果，初步设计了8种含能性质较好的目标化合物。采用不同理论方法对其生成热、密度和爆轰性能进行了预测，为高氮含能化合物的试验合成提供了素材和理论参考。
5．根据Hiskey等人对高氮含能化合物3，6-双(叠氮基)-1，2，4，5-四嗪中的叠氮基环化处理，采用密度泛函理论对叠氮基的环化机理进行了初步的理论分析，给出了实验中只生成一种产物的可能原因。
6．理论计算中采用密度泛函理论对研究对象进行结构优化和频率计算，运用自然键轨道(NBO)理论和分子中的原子(AIM)理论进行电子结构分析，采用原子化方案(atomic scheme)、Monte-Carlo方法和VLW状态方程分别计算了标准气态生成热、分子密度及爆速和爆压。
The main work of this dissertation is as follows:
1. The constituent units of high-nitrogen compounds have been classified as structural units, connecting units and substitutional radicals at base of many references. And the current experimental and theoretical studies for high-nitrogen compounds are reviewed. At last, we take tetrzine compounds as main work of this dissertation.
2. For distinctly understanding the mutual influence between the structural units, a series of compounds from five and six-membered C-N heterocycle substituting the tetrazine ring are designed. These several types of compounds are studied by means of the quantum chemistry calcualtions and discussed the influence of the structural units upon the main performance (heat of formation, density, velocity and pressure of detonation) and found out the best combination of performance.
3. Nine kinds of compounds from the connecting units (-N=N-) and substitutional radicals (-NH_2、-N_3) substituting the tetrazine are designed and analysed their electronic structures, different radicals' contribution to heat of formation, velocity and pressure of detonation.
4. At last, we design 8 kinds of energetic compounds with good properties on the basis of preferable high-nitrogen materials (BTATz and DAAT) and the results of above analysis. Then heat of formation, density, velocity and pressure of detonation were calculated by means of different theoretical methods. And the results can offer the theoretical reference for synthesize of high-nitrogen compounds.
5. At the base of experimental results for cyclization of the azide group 3, 6-bis(azide) -s-tetrazine, we primaryily studied the cyclization process by means of theoretical methods, gave the possible reason for only one product.
6. The optimization and the vibrational frequencies were calculated by the density functional theory for all the molucules. The electronic structures were analyzed by means of natural bond orbital (NBO) and atom in the molecule (AIM). The calculations about the standard gaseous heat of formation, molecular density, velocity and pressure of detonation were respectively used by the atomic scheme, the method of Monte-Carlo and VLW state equations.
1．在总结分析大量文献的基础上对高氮化合物的组成单元进行了分类，主要分为结构单元、连接单元和取代基；对高氮化合物的实验和理论最新研究进展进行了综述，提出了以1，2，4，5-四嗪类化合物作为本论文的主要研究内容。
2．为了更清楚的了解结构单元之间的相互影响，设计了六元氮杂环和五元氮杂环取代1，2，4，5-四嗪得到了一系列化合物，采用量子化学计算方法对它们进行了详细的理论研究，讨论了各种氮杂环的改变对四嗪类化合物性能(包括生成热、密度以及爆速和爆压等)的影响，并找出爆轰性能较好的结构单元组合。
3．设计了连接桥(-N=N-)和取代基(-NH_2、-N_3)与1，2，4，5-四嗪环直接相连得到9种化合物，分析和讨论了它们的电子结构以及不同基团对生成热、爆速和爆压的贡献。
4．根据实验中已经合成且性能较好的高氮含能化合物BTATz和DAAT的结构特点和结构与性能关系的理论分析结果，初步设计了8种含能性质较好的目标化合物。采用不同理论方法对其生成热、密度和爆轰性能进行了预测，为高氮含能化合物的试验合成提供了素材和理论参考。
5．根据Hiskey等人对高氮含能化合物3，6-双(叠氮基)-1，2，4，5-四嗪中的叠氮基环化处理，采用密度泛函理论对叠氮基的环化机理进行了初步的理论分析，给出了实验中只生成一种产物的可能原因。
6．理论计算中采用密度泛函理论对研究对象进行结构优化和频率计算，运用自然键轨道(NBO)理论和分子中的原子(AIM)理论进行电子结构分析，采用原子化方案(atomic scheme)、Monte-Carlo方法和VLW状态方程分别计算了标准气态生成热、分子密度及爆速和爆压。
The main work of this dissertation is as follows:
1. The constituent units of high-nitrogen compounds have been classified as structural units, connecting units and substitutional radicals at base of many references. And the current experimental and theoretical studies for high-nitrogen compounds are reviewed. At last, we take tetrzine compounds as main work of this dissertation.
2. For distinctly understanding the mutual influence between the structural units, a series of compounds from five and six-membered C-N heterocycle substituting the tetrazine ring are designed. These several types of compounds are studied by means of the quantum chemistry calcualtions and discussed the influence of the structural units upon the main performance (heat of formation, density, velocity and pressure of detonation) and found out the best combination of performance.
3. Nine kinds of compounds from the connecting units (-N=N-) and substitutional radicals (-NH_2、-N_3) substituting the tetrazine are designed and analysed their electronic structures, different radicals' contribution to heat of formation, velocity and pressure of detonation.
4. At last, we design 8 kinds of energetic compounds with good properties on the basis of preferable high-nitrogen materials (BTATz and DAAT) and the results of above analysis. Then heat of formation, density, velocity and pressure of detonation were calculated by means of different theoretical methods. And the results can offer the theoretical reference for synthesize of high-nitrogen compounds.
5. At the base of experimental results for cyclization of the azide group 3, 6-bis(azide) -s-tetrazine, we primaryily studied the cyclization process by means of theoretical methods, gave the possible reason for only one product.
6. The optimization and the vibrational frequencies were calculated by the density functional theory for all the molucules. The electronic structures were analyzed by means of natural bond orbital (NBO) and atom in the molecule (AIM). The calculations about the standard gaseous heat of formation, molecular density, velocity and pressure of detonation were respectively used by the atomic scheme, the method of Monte-Carlo and VLW state equations.
引文
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2 Hiskey M, Chavez D, et al. Progress in high-nitrogen chemistry in explosives, propellants and pyrotechnics A. Proc. 27th International Pyrotechnics Seminar[C], July 16～21, USA: Colorado, 2000: 3～14.
3 Huynh M. H. V, Hiskey M, Pollard C.J., et al. 4,4',6,6'-Tetra-Substituted Hydrazo- and Azoo-1, 3, 5-Triazines J. Energ. Mater. 2004, 22, 217～229.
4 Huynh M. H.V, Hiskey M, Ernest L, et al. Polyazido High-Nitrogen Compounds: Hydrazoand Azo-1,3,5-triazine[J]. Angew. Chem. Int. Ed. 2004, 43: 4924～4928
5 Neutz J, Grosshardt O, Schaufele S, et al. Synthesis, characterization and thermal behaviour of guanidinium-5-aminotetrazolate (GA)-A new nitrogen-rich compound[J]. Propellants, Explosives, Pyrotechnics. 2003, 28: 181～188.
6 Churakov A.M, Smimov O.Y, Ioffe S.L, et al.Benzo-1,2,3,4-tetrazine 1,3-Dioxides: Synthesis and NMR Study [J]. Eur. J. Org. Chem. 2002: 2342～2349.
7 Hiskey M, Chavez D. Insensitive high-nitrogen compounds[R]. NTIS No: DE220012776133, 2001.
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