3,5-dinitro-1,2,4-triazole ammonium salt

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3,5-dinitro-1,2,4-triazole ammonium salt
• 英文别名: ammonium 3,5-dinitro-1,2,4-triazolate；ammonium 3,5-nitro-1,2,4-tetrazolate；amminoum 3,5-dinitro-1,2,4-triazole；3,5-dinitro-1,2,4-triazoleammonium；A⁺DNT；azane;3,5-dinitro-1H-1,2,4-triazole
• 化学式: C₂HN₅O₄*H₃N
• 分子量: 176.092
• InChiKey: LXZANYUADMGNPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-dinitro-1,2,4-triazole ammonium salt 在 一水合肼 、 盐酸 作用下， 反应 2.0h， 以76.1%的产率得到(9ci)-5-硝基-1H-1,2,4-噻唑-3-胺
  参考文献：
  名称：

  N-氨基化合物的合成和结构表征

  摘要：

  富含氮的杂环基化合物最常用于含能化合物，因为它们比碳环类似物具有更高的正形成热、密度和氧平衡。富氮化合物形成了一类独特的高能材料，其能量来源于其高形成热，直接归因于大量固有的高能 CN、NN、C=N 和 N=N 键。与通常的碳环类似物相比，更少量的氢和碳有助于更好的氧平衡，它们的分解产物中更高的百分比将是 N2。吡唑、三唑、四唑、四嗪、呋喃和呋喃衍生物由于它们的高形成热而成为有趣的高能材料，高氮含量和良好的热稳定性源于其芳香性。最近，偶氮基团与高氮杂芳环的结合得到了广泛的研究，因为偶氮键不仅使高氮化合物脱敏，而且显着增加了高氮化合物的形成热，例如 3,3'-偶氮双 (6-氨基-1,2,4,5-四嗪), 4,4'-偶氮二-1,2,4三唑, 1,1'-偶氮二(3-硝基-1,2,4,5-四唑), 1, 1'-azobis1,2,3-triazole, 4,4',6,6'-tetra(azido)azo-1

  DOI：

  10.14233/ajchem.2014.16529
• 作为产物：
  描述：

  3,5-Dinitro-1,2,4-triazol 在 ammonium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 以17.1 g的产率得到3,5-dinitro-1,2,4-triazole ammonium salt
  参考文献：
  名称：

  基于 5-Azido-3-nitro-1, 2,4-triazolate 阴离子的高能材料

  摘要：

  本研究介绍了 5-叠氮基-3-硝基-1H-1, 2,4-三唑 (1) 的高产率和高纯度制备，从市售化学品开始，分三步合成。此外，几种富含金属和氮的盐与钠 (3)、钾 (4)、铯 (5)、银 (6)、铅 (7)、铵 (8)、胍 (9) 和氨基胍 (10)由简单的酸碱反应制备。所有化合物都通过各种手段进行了充分表征，包括振动（IR、拉曼）和多核（1H、13C、14N、15N）NMR 光谱、质谱和 DSC。此外，通过单晶 X 射线衍射确定了 7 的结构。根据 BAM 标准确定对各种外部刺激（冲击、摩擦、静电放电）的敏感性。

  DOI：

  10.1002/zaac.201300203

文献信息

• Amination of energetic anions: high-performing energetic materials
  作者：Thomas M. Klapötke、Davin G. Piercey、Jörg Stierstorfer

  DOI：10.1039/c2dt30684k

  日期：——

  The new energetic materials 2-amino-5-nitrotetrazole (ANT, 1), 1-amino-3,4-dinitro-1,2,4-triazole (ADNT, 2), and both 1,1′-diamino-5,5′-bistetrazole and 1,2′-diamino-5,5′-bistetrazole (11DABT, 3 and 12DABT, 4) have been prepared by the amination of the parent anion with O-tosylhydroxylamine. The 5-H-tetrazolate anion has also been aminated using hydroxylamine O-sulfonic acid to both 1-aminotetrazole and 2-aminotetrazole (1AT, 5 and 2AT, 6). The prepared materials have been characterized chemically (XRD (1–4, 6·AtNO222, 8), multinuclear NMR, IR, Raman) and as explosives (mechanical and electrostatic sensitivity) and their explosive performances calculated using the EXPLO5 computer code. The prepared N-amino energetic materials, which can also be used as new ligands for high energy-capacity transition metal complexes, exhibit high explosive performances (in the range of hexogen and octogen) and a range of sensitivities from low to extremely high.

  新的高能材料 2-氨基-5-硝基四氮唑（ANT，1）、1-氨基-3,4-二硝基-1,2,4-三氮唑（ADNT，2）以及 1,1′-二氨基-5,5′-双四唑和 1、2′-二氨基-5,5′-双四唑（11DABT, 3 和 12DABT, 4）都是通过母阴离子与 O-对甲苯磺酸羟胺胺化制备的。5-H 四氮唑阴离子也用羟胺 O-磺酸胺化成了 1-氨基四氮唑和 2-氨基四氮唑（1AT, 5 和 2AT,6）。已对制备的材料进行了化学表征（XRD（1-4、6-AtNO222、8）、多核 NMR、IR、Raman）和爆炸表征（机械和静电敏感性），并使用 EXPLO5 计算机代码计算了它们的爆炸性能。所制备的 N-氨基高能材料也可用作高能量过渡金属配合物的新配体，具有很高的爆炸性能（在六原和八原范围内）和从低到极高的灵敏度。
• Synthesis of energetic salts containing three heterocyclic anions by a one-pot condensation reaction
  作者：Panpan Peng、Baoping Hu、Feipeng Lu、Yao Du、Chaofeng Zhao、Hui Su、Pengcheng Zhang、Shenghua Li、Siping Pang

  DOI：10.1039/c9nj03857d

  日期：——

  energetic ion salts containing three heterocyclic anions via a one-step one-pot condensation reaction. The proposed strategy is based on aldehydes, aminoguanidine salts, and heterocyclic energetic ionic salts. In this work, energetic salt 1 containing three 5-nitrotetrazole anions and energetic salt 2 containing three 3,5-dinitro-1,2,4-triazole anions were successfully synthesized. The results of NMR, IR,

  杂环高能盐由于其出色的分子设计性能而被广泛用于高能材料。通常，大多数无机或有机阴离子高能离子盐最多仅包含一个阴离子或两个阴离子。迄今为止，尚未报道含有三种有机高能阴离子的高能离子盐。在这项研究中，我们开发了一种通过一步式一锅缩合反应制备包含三个杂环阴离子的高能离子盐的新方法。提出的策略基于醛，氨基胍盐和杂环高能离子盐。在这项工作中，有活力盐1包含三个5- nitrotetrazole阴离子和充满活力的盐2已成功合成了包含三个3,5-二硝基-1,2,4-三唑阴离子的阴离子。NMR，IR和MS的结果证明产物（1和2）含有三个杂环阴离子。高能测试结果表明，产物1和2的分解温度极高（250°C和308°C），灵敏度低（对于1和2而言，FS> 360 N，IS> 40 J）。同时，它们的爆炸速度（7306 ms -1和7375 ms -1）和爆炸压力（18.3 GPa和19.7 GPa）优于TNT。
• Thermal Decomposition Studies on NTO and NTO/TNT
  作者：Jimmie C. Oxley、James L. Smith、ZunLiang Zhou、Robert L. McKenney

  DOI：10.1021/j100025a047

  日期：1995.6

  The thermal decomposition of 5-nitro-2,4-dihydro-3H-1,2,4-triazol-3-one (NTO) was examined over the temperature range 220-280 degrees C using both neat NTO and NTO in aqueous and methanol solutions. The decomposition of NTO in the presence of 2,4,6-trinitrotoluene (TNT) was also examined. Activation parameters were calculated for all thermolyses. When mixtures of NTO and TNT were decomposed, the decomposition rate of both components was enhanced. Additives such as NO2, ammonia, nitric acid, and ammonium nitrate also accelerated the decomposition of NTO and of TNT. Decomposition of deuterated NTO neat and in solution was noticeably slower than that of proteo-NTO, indicative of an intramolecular deuterium kinetic isotope effect (DKIE). An intermolecular DKIE was-also observed when NTO was decomposed in deuterated solvent or in a mixture with TNT-d(3). It was concluded that the rate-determining step in at least one NTO thermolysis pathway involved hydrogen transfer to the nitro group followed by subsequent:loss of HONO. This mechanism is believed to be dominant at low temperatures, while at high temperatures C-NO2 homolysis is probably a competitive decomposition pathway. Decomposition products from NTO thermolysis, neat, in solution, and in admixture with TNT, are reported for the first time. The condensed-phase thermolyses produced small quantities of 2,4-dihydro-3H-1,2,4-triazol-3-one (TO) and large amounts of an intractable tar for which the elemental ratio was roughly that of TO. Because TO was observed as a NTO decomposition product, its thermal decomposition behavior was examined in the same fashion as that of NTO. LikeNTO/TNT mixtures, TO/TNT mixtures exhibited mutual destabilization. However, unlike NTO, TO exhibited neither an internor ari intramolecular DKIE, and its decomposition rate was unaffected by the presence of NO2. The elemental analysis of the TO residue differed from that of thermolyzed NTO. It was concluded that TO, while formed in the decomposition of NTO, was not an intermediate in the principal NTO decomposition pathway. Furthermore, while it appeared that NTO and TO promoted TNT decom;position by the same mechanism, hydrogen transfer to an arerie nitro group, the mode by which TNT enhanced the decomposition of the two triazolone rings, differed. The kinetics and products of decomposition of eight other triazole-like rings were examined. Thermal stability was related to ring substitution; rings with NO2 and NH2 substituents decomposed more rapidly at 270 degrees C than those with O or H on carbon. The enhancement of decomposition under NO2 atmosphere was observed only on rings substituted with NH2 or O groups, suggesting the carbonyl of NTO is the point subject to NO2 attack. Hydrogen transfer to the nitro of NTO was supported by the observation that only rings substituted with either NO2 or NH2 exhibited an intermolecular DKIE.
• Energetic Materials Based on the 5-Azido-3-nitro-1, 2,4-tri­azolate Anion
  作者：Dániel Izsák、Thomas M. Klapötke、Regina Scharf、Jörg Stierstorfer

  DOI：10.1002/zaac.201300203

  日期：2013.8

  This study presents the preparation of 5-azido-3-nitro-1H-1, 2,4-triazole (1) in both good yield and high purity, starting from commercially available chemicals in a three step synthesis. Furthermore, several metal and nitrogen-rich salts with sodium (3), potassium (4), cesium (5), silver (6), lead (7), ammonium (8), guanidinium (9), and aminoguanidinium (10) were prepared by simple acid-base reactions

  本研究介绍了 5-叠氮基-3-硝基-1H-1, 2,4-三唑 (1) 的高产率和高纯度制备，从市售化学品开始，分三步合成。此外，几种富含金属和氮的盐与钠 (3)、钾 (4)、铯 (5)、银 (6)、铅 (7)、铵 (8)、胍 (9) 和氨基胍 (10)由简单的酸碱反应制备。所有化合物都通过各种手段进行了充分表征，包括振动（IR、拉曼）和多核（1H、13C、14N、15N）NMR 光谱、质谱和 DSC。此外，通过单晶 X 射线衍射确定了 7 的结构。根据 BAM 标准确定对各种外部刺激（冲击、摩擦、静电放电）的敏感性。
• Synthesis and Structural Characterization of N-Amino Compounds
  作者：Ya-Nan Li、Ning Liu、Peng-Fei Su、Ying-Lei Wang、Zhong-Xue Ge、Hui Li、Bo-Zhou Wang

  DOI：10.14233/ajchem.2014.16529

  日期：——

  better oxygen balance than normally is found with their carbocyclic analogues, a higher percentage of their decomposition products will be N2. Pyrazole, triazole, tetrazole, tetrazine, furazan and furoxan derivatives are interesting high energy materials due to their highly positive heats of formation, high nitrogen content and good thermal stability deriving from their aromaticity. Recently, the combination

  富含氮的杂环基化合物最常用于含能化合物，因为它们比碳环类似物具有更高的正形成热、密度和氧平衡。富氮化合物形成了一类独特的高能材料，其能量来源于其高形成热，直接归因于大量固有的高能 CN、NN、C=N 和 N=N 键。与通常的碳环类似物相比，更少量的氢和碳有助于更好的氧平衡，它们的分解产物中更高的百分比将是 N2。吡唑、三唑、四唑、四嗪、呋喃和呋喃衍生物由于它们的高形成热而成为有趣的高能材料，高氮含量和良好的热稳定性源于其芳香性。最近，偶氮基团与高氮杂芳环的结合得到了广泛的研究，因为偶氮键不仅使高氮化合物脱敏，而且显着增加了高氮化合物的形成热，例如 3,3'-偶氮双 (6-氨基-1,2,4,5-四嗪), 4,4'-偶氮二-1,2,4三唑, 1,1'-偶氮二(3-硝基-1,2,4,5-四唑), 1, 1'-azobis1,2,3-triazole, 4,4',6,6'-tetra(azido)azo-1