potassium 1,1,3,3-tetracyano propenide | 36589-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: potassium 1,1,3,3-tetracyano propenide
• 英文别名: potassium 1,1,3,3-tetracyanopropenide；propene-1,1,3,3-tetracarbonitrile; potassium-compound；Propen-1,1,3,3-tetracarbonitril; Kalium-Verbindung；Kalium-(1,1,3,3,-tetracyan-propenid)；Potassium;prop-1-ene-1,1,3,3-tetracarbonitrile
• CAS: 36589-04-5
• 化学式: C₇HN₄*K
• 分子量: 180.21
• InChiKey: WPUDDIKRBWGXNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.41
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  potassium 1,1,3,3-tetracyano propenide 以 氯仿 为溶剂， 生成 N,N-Dimethyl-N'-phenyl-N''-((E)-2,4,4-tricyano-1-phenylamino-buta-1,3-dienyl)-guanidine
  参考文献：
  名称：

  Kukhar',V.P.; Pavlenko,N.G., Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 33 - 35

  摘要：

  DOI：

文献信息

• Synthesis and Characterization of a Dinuclear Nitrogen-Rich Ferrocenyl Ligand and Its Ionic Coordination Compounds and Their Catalytic Effects During Combustion
  作者：Liping Jiang、Manman Liu、Lei Xu、Tuanrui Dong、Jizhen Li、Guofang Zhang

  DOI：10.1002/zaac.201800417

  日期：2019.1.31

  deal with these drawbacks, a novel dinuclear nitrogen‐rich ferrocene derivative, 4‐amino‐3,5‐bis(4‐ferrocenyl‐1,2,3‐triazolyl‐1‐methyl)‐1,2,4‐triazole (BFcTAZ) and its twenty seven ionic coordination compounds, [M2(BFcTAZ)2(H2O)4]mXn·xH2O (M = Cr3+, Mn2+, Fe3+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+ and Pb2; X = polycyano anions), were synthesized and characterized by FT‐IR, UV/Vis, and elementary analysis. Crystal

  烷基二茂铁基燃烧速率催化剂（BRC）表现出明显的迁移趋势和高挥发性，因此导致复合固体推进剂在燃烧过程中的性能较差。为了解决这些缺点，提出了一种新型的双核富氮二茂铁衍生物4-氨基-3,5-双（4-二茂铁基1,2,3-三唑基-1-甲基）1,2,4-三唑（ BFcTAZ）及其二十七个离子配位化合物[ M 2（BFcTAZ）2（H 2 O）4 ] m X n · x H 2 O（M = Cr 3+，Mn 2 +，Fe 3+，Co 2+， 你2+，Cu 2 +，Zn 2 +，Cd 2+和Pb 2；X合成并通过FT-IR，UV / Vis和元素分析进行​​表征。通过单晶X射线衍射进一步证实了BFcTAZ的晶体结构，并提出了新配合物的一般分子结构。通过TG技术证实了它们的高热稳定性。循环伏安法研究表明，新化合物是多种氧化还原系统。通过DSC技术测定了它们对某些常见氧化剂的热降解的影响。结果表明，大多数新的配合物对AP，RDX和1
• Ionic Ferrocene‐Based Burning‐Rate Catalysts with Polycyano Anions: Synthesis, Structural Characterization, Migration, and Catalytic Effects during Combustion
  作者：Xuelin Liu、Jizhen Li、Fuqiang Bi、Weiqiang Zhang、Guofang Zhang、Ziwei Gao

  DOI：10.1002/ejic.201403023

  日期：2015.3

  Alkylferrocene‐based burning‐rate (BR) catalysts, have a high tendency to migrate during curing and storage due to their neutral and nonpolar nature. To overcome these drawbacks, fifteen novel ionic compounds, 1‐(ferrocenylmethyl)imidazolium paired with polycyano anions, were synthesized and characterized. The structures of eleven of the compounds were confirmed by single‐crystal X‐ray diffraction

  由于烷基二茂铁的燃烧速率（BR）催化剂具有中性和非极性性质，因此在固化和存储期间极易迁移。为克服这些缺点，合成并表征了15种新型离子化合物，即1-（二茂铁基甲基）咪唑鎓与多氰基阴离子配对。单晶X射线衍射证实了11种化合物的结构。化合物1在四方空间群I4（1）/ a中结晶；2，12和15在斜空间群结晶P 2 1 / ç，和3的单斜空间群P 2 1 / Ñ; 4，6 - 8，13和14中的三斜晶系空间群结晶P。循环伏安法研究表明，大多数化合物都表现出准可逆的氧化还原系统。化合物1 – 10具有高的热稳定性（> 190°C）。迁移研究表明，这些化合物是低迁移材料。通过差示扫描量热法（DSC）和热重分析（TG）技术，评估了这些化合物催化的高氯酸铵（AP），正己烷（RDX）和正辛酯（HMX）的热降解。结果表明，使用新化合物作为添加剂时，AP的分解峰温度急剧下降，并且AP释放的热量显着增加（5 wt。
• Ionic Ferrocenyl Compounds Containing Polycyano Anions. Synthesis, Structures, and Effects on Thermal Decomposition of Core Components of Solid Propellants
  作者：Xiaoni Gao、Jizhen Li、Yang Luo、Chunxiao Li、Fuqiang Bi、Weiqiang Zhang、Guofang Zhang、Ziwei Gao

  DOI：10.1002/zaac.201400467

  日期：2015.2

  For lowering high migration tendency of alkyl‐substituted ferrocenes as burning‐rate catalysts in composite solid propellants, eight new ionic ferrocenyl compounds, [FcCH2N(CH3)2(CnH2n+1]+X– (Fc = ferrocenyl; X– = 1,1,3,3‐tetracyanopropenide; n = 3–10; consequently numbered as 1–8), were synthesized and characterized by 1H NMR, 13C NMR, FT‐IR and UV/Vis spectroscopy as well as elementary analysis.

  为了降低烷基取代的二茂铁作为固体推进剂中燃烧速率催化剂的高迁移趋势，使用了八种新的离子二茂铁化合物[FcCH 2 N（CH 3）2（C n H 2 n +1 ] + X –（Fc =合成了二茂铁基；X – = 1,1,3,3-四氰基丙烯；n = 3-10；因此编号为1 – 8），并通过1 H NMR，13 C NMR，FT-IR和UV / Vis光谱进行了表征以及另外如元素分析。，的结构1，通过单晶X射线衍射分析确定了3和5，并通过密度泛函理论计算（DFT）研究了它们的阳离子。1，3，及5结晶在三斜晶系空间群P。1 – 6显示出很高的热稳定性（> 166°C），而化合物7和8表现出一定程度的波动性。循环伏安法研究表明，每种盐都表现出二茂铁基的准可逆氧化还原波。新化合物对高氯酸铵（AP），1,3,5-三硝基-1,3,5-三氮杂环己烷（RDX）和1,2,5,7-四硝基-1,3，通过DSC技术研究了5
• Ionic binuclear ferrocenyl compounds containing 1,1,3,3-tetracyanopropenide anions – synthesis, structural characterization and catalytic effects on thermal decomposition of main components of solid propellants
  作者：Dongmei Zhao、Jizhen Li、Fuqiang Bi、Yahui Yang、Xiaoni Gao、Weiqiang Zhang、Guofang Zhang、Ziwei Gao

  DOI：10.1515/znb-2014-0251

  日期：2015.5.1

  Alkyl-substituted ferrocenes are typical burning-rate catalysts in composite solid propellants, but their high migration tendency and volatility has impeded their extensive applications. By introducing the concept of ionic energetic compounds, eight new ionic binuclear ferrocenyl compounds, [FcCH₂N(CH₃)₂(CH₂) _n N(CH₃)₂CH₂Fc]²⁺ (X^– ₂) (Fc = ferrocenyl; X^– = 1,1,3,3-tetracyano propenide; n = 3–10; the compounds being numbered consecutively 1–8), were prepared and characterized. The molecular structures of 1, 2, and 4 were determined by single-crystal X-ray diffraction, and their cations were studied by density functional theory calculations (DFT). Compounds 1–5 show high thermal stability but 6–8 are slightly volatile. The results of cyclic voltammetry studies suggest that each salt exhibits a quasireversible redox system. Catalytic effects of the new salts on thermal degradation of ammonium perchlorate (AP), 1,3,5-trinitro-1,3,5-triaza-cyclo-hexane (RDX), and 1,2,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX), have been investigated by DSC and/or TG methods. The results show that the new compounds can bring the peak temperatures of both AP and RDX down significantly and enhance their heat release dramatically, indicating that the ferrocenyl salts possess high catalytic efficiency for the thermal decomposition of AP and RDX. Their catalytic activities are nearly equal to or higher than that of the corresponding nitrates and picrates, as well as their mononuclear counterparts. Compound 6 also efficiently catalyzes the thermal decomposition of hydroxyl-terminated polybutadiene (HTPB) and 1:1 mixtures of HTPB and AP.

  摘要：烷基取代的二茂铁是复合固体推进剂中典型的燃烧速率催化剂，但其高迁移倾向和挥发性阻碍了其广泛应用。通过引入离子能化合物的概念，制备并表征了八种新的离子双核二茂铁化合物 [FcCH₂N(CH₃)₂(CH₂)_nN(CH₃)₂CH₂Fc]²⁺ (X^–₂) (Fc = 二茂铁基；X^– = 1,1,3,3-四氰基丙烯酸根；n = 3-10；化合物按顺序编号为1-8)。通过单晶X射线衍射确定了化合物1、2和4的分子结构，并通过密度泛函理论计算（DFT）研究了它们的阳离子。化合物1-5具有高热稳定性，但6-8稍具挥发性。循环伏安法研究结果表明，每种盐都表现出准可逆的氧化还原系统。通过DSC和/或TG方法研究了新盐对过氯酸铵（AP）、1,3,5-三硝基-1,3,5-三氮杂环己烷（RDX）和1,2,5,7-四硝基-1,3,5,7-四氮杂环辛烷（HMX）的热分解的催化效果。结果表明，新化合物可以显著降低AP和RDX的峰值温度，并显著提高它们的放热量，表明二茂铁盐对AP和RDX的热分解具有高催化效率。它们的催化活性几乎等于或高于相应的硝酸盐和偏硝酸盐，以及它们的单核对应物。化合物6还有效地催化了羟基终止的聚丁二烯（HTPB）和HTPB和AP的1:1混合物的热分解。
• Dinuclear (Ferrocenylmethyl)imidazolium Ionic Compounds with Polycyano Anions. Characterization, Migration, and Effects during Combustion
  作者：Manman Liu、Ersha Shao、Kai Zhao、Jizhen Li、Ziwei Gao、Guofang Zhang

  DOI：10.1002/zaac.201700120

  日期：2017.7.17

  Alkyl-substituted ferrocene-based burning rate catalysts exhibit high migration and volatility during curing process and prolonged storage of the composite solid propellants. To deal with the drawbacks twenty-one dinuclear (ferrocenylmethyl)imidazolium compounds paired with polycyano anions, were synthesized and characterized by 1H NMR, 13C NMR, UV/Vis, elementary analysis, and both 2 and 11 were further

  烷基取代的二茂铁基燃烧速率催化剂在固化过程和复合固体推进剂的长期储存过程中表现出高迁移率和挥发性。为了解决这些缺点，合成了与多氰基阴离子配对的 21 种双核（二茂铁基甲基）咪唑鎓化合物，并通过 1H NMR、13C NMR、UV/Vis、元素分析进行​​了表征，2 和 11 均通过单晶 X 进一步表征-射线衍射。迁移试验表明该化合物具有优异的抗迁移能力。循环伏安法结果表明它们是准可逆或不可逆的氧化还原系统。TG/DSC 分析表明该化合物具有高度的热稳定性。它们对高氯酸铵 (AP) 和 1,3,5-trinitro-1,3 热分解的影响，另外检查了5-三氮杂环己烷(RDX)。结果表明，新化合物对AP和RDX在燃烧过程中的热分解有很强的影响。13和21在增加AP的放热方面均优于双二茂，可作为复合固体推进剂中双二茂的替代品。