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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >The nitration pattern of energetic 3,6-diamino-1,2,4,5-tetrazine derivatives containing azole functional groups
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The nitration pattern of energetic 3,6-diamino-1,2,4,5-tetrazine derivatives containing azole functional groups

机译：含唑官能团的高能3,6-二氨基-1,2,4,5-四嗪衍生物的硝化模式

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摘要

One of the successful strategies for the design of promising new energetic materials is the incorporation of both fuel and oxidizer moieties into the same molecule. Therefore, during recent years, synthesis of various nitro-azole derivatives, as compounds with a more balanced oxygen content, has become very popular. In the framework of this effort, we studied nitration of N-3,N-6-bis(1H-tetrazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine (BTATz; 5) and its alkylated derivative N-3,N-6-bis(2-methyl-2H-tetrazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine 12, using a N-15-labeled nitration agent and monitoring and analyzing products of these reactions by N-15 NMR. It was seen that the nitration of both compounds takes place only on the exocyclic ("bridging") secondary amine groups. Possible tetranitro derivative isomers N,N'-(1,2,4,5-tetrazine-3,6-diyl)bis(N-(1-nitro-1H-tetrazol-5-yl)-nitramide) 6 and N,N'-(1,2,4,5-tetrazine-3,6-diyl)bis(N-(2-nitro-2H-tetrazol-5-yl)nitramide) 7, both of which have OB = 0% and calculated VODs of 9790 and 9903 m s(-1), respectively, could not be observed in the reaction mixtures, during the in situ N-15 NMR monitoring of nitration of 5, using N-15-labeled nitrating agents. Following a similar strategy, a new analog of BTATz - N-3,N-6-Bis(1H-1,2,4-triazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine 15 was obtained and its nitration was studied. The reaction of 15 with a HNO3-Ac2O nitration mixture resulted in the formation of a new N-3,N-6-bis(3-nitro-1H-1,2,4-triazol-5-yl)-1,2,4,5-tetrazine-3,6-diamine derivative 20 in a moderate yield. Structures and properties of 15 (in the form of its perchlorate salt, 16) and 20 were measured by FTIR, multinuclear NMR, MS, DSC and X-ray crystallography. It is important to note that compound 20 exhibits exothermic decomposition at 302 degrees C (DSC) and >353 N (sensitivity to friction), making it a highly-promising thermally-insensitive energetic material for further development.
机译：设计有前途的新的高能材料的成功策略之一是将燃料和氧化剂部分都结合到同一分子中。因此，近年来，作为具有更平衡的氧含量的化合物的各种硝基唑衍生物的合成已变得非常流行。在这项工作的框架内，我们研究了N-3，N-6-双（1H-四唑-5-基）-1,2,4,5-四嗪-3,6-二胺（BTATz; 5）的硝化作用及其烷基化衍生物N-3，N-6-双（2-甲基-2H-四唑-5-基）-1,2,4,5-四嗪-3,6-二胺12，使用N-15-标记的硝化剂，并通过N-15 NMR监测和分析这些反应的产物。可见两种化合物的硝化仅在环外（“桥”）仲胺基团上进行。可能的四硝基衍生物异构体N，N'-（1,2,4,5-tetrazine-3,6-diyl）bis（N-（1-nitro-1H-tetrazol-5-yl）-nitramide）6和N， N'-（1,2,4,5-tetrazine-3,6-diyl）bis（N-（2-nitro-2H-tetrazol-5-yl）nitramide）7，它们的OB = 0％，且在使用N-15标记的硝化剂进行原位N-15 NMR监测5的硝化反应过程中，无法在反应混合物中观察到分别计算的9790和9903 ms（-1）的VOD。遵循类似的策略，BTATz的新类似物-N-3，N-6-Bis（1H-1,2,4-三唑-5-基）-1,2,4,5-四嗪3,6-获得二胺15并研究其硝化作用。 15与HNO3-Ac2O硝化混合物的反应导致形成新的N-3，N-6-双（3-硝基-1H-1,2,4-三唑-5-基）-1,2 ，4,5-四嗪-3,6-二胺衍生物20的产率中等。通过FTIR，多核NMR，MS，DSC和X射线晶体学测量了15（以其高氯酸盐形式，16）和20的结构和性质。重要的是要注意，化合物20在302摄氏度（DSC）和> 353 N（对摩擦的敏感性）下表现出放热分解，使其成为高度有前途的对热不敏感的高能材料，可供进一步开发。

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