potassium 3,5-bis(nitroamino)-1,2,4-triazolide | 105555-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: potassium 3,5-bis(nitroamino)-1,2,4-triazolide
• 英文别名: N³,N⁵-dinitro-1H-[1,2,4]triazole-3,5-diyldiamine; potassium-salt；N³,N⁵-Dinitro-1H-[1,2,4]triazol-3,5-diyldiamin; Kalium-Salz
• CAS: 105555-73-5
• 化学式: C₂H₂N₇O₄*K
• 分子量: 227.181
• InChiKey: GAJGHPQWWOAGGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.39
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  153.98
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  potassium 3,5-bis(nitroamino)-1,2,4-triazolide 在 氢氧化钾 作用下， 以 水 为溶剂， 以96%的产率得到3,5-bis(nitroamino)-1,2,4-triazole dipotassium salt
  参考文献：
  名称：

  2-硝基胍衍生物：V.3，5-双（硝基氨基）-1，2，4-三唑盐的合成和结构。3,5-双（硝基氨基）-1,2,4-三唑的酸碱性质

  摘要：

  Heterocyclization of hydrazine-1,2-bis(N-2-nitrocarboximidamide) and salts derived therefrom provides a procedure for the synthesis of 3,5-bis(nitroamino)-1,2,4-triazole salts. The presence of two acceptor nitroamino groups conjugated with the triazole ring considerably enhances the acidity of 3,5-bis(nitroamino)-1,2,4-triazole (pK(a)(1) = -2.0, pK(a)(2) = 4.8, pK(a)(3) = 10.6) as compared to mononitroaminotriazole, so that formation of salts with the corresponding dianion becomes possible.

  DOI：

  10.1023/b:rujo.0000036077.24894.51
• 作为产物：
  描述：

  aminoguanidinium 3,5-bis(nitroamino)-1,2,4-triazolide 在 potassium hydrogencarbonate 作用下， 以 水 为溶剂， 以82%的产率得到potassium 3,5-bis(nitroamino)-1,2,4-triazolide
  参考文献：
  名称：

  2-硝基胍衍生物：V.3，5-双（硝基氨基）-1，2，4-三唑盐的合成和结构。3,5-双（硝基氨基）-1,2,4-三唑的酸碱性质

  摘要：

  Heterocyclization of hydrazine-1,2-bis(N-2-nitrocarboximidamide) and salts derived therefrom provides a procedure for the synthesis of 3,5-bis(nitroamino)-1,2,4-triazole salts. The presence of two acceptor nitroamino groups conjugated with the triazole ring considerably enhances the acidity of 3,5-bis(nitroamino)-1,2,4-triazole (pK(a)(1) = -2.0, pK(a)(2) = 4.8, pK(a)(3) = 10.6) as compared to mononitroaminotriazole, so that formation of salts with the corresponding dianion becomes possible.

  DOI：

  10.1023/b:rujo.0000036077.24894.51

文献信息

• ——
  作者：A. A. Astrat'yev、D. V. Dashko、L. L. Kuznetsov

  DOI：10.1023/a:1026003700547

  日期：——

  1,2-Dinitroguanidine is a product of nitroguanidine nitration with nitric acid and its mixtures with sulfuric acid and oleum. It is a diacid (pK(a), 1.11, similar to 11.5) and at the same time a weak base undergoing protonation at the nitrogen of the amino group (pK(BH) + -5.81). The decomposition kinetics of 1,2-dinitro-guanidine was studied by spectrophotometric method both in acid and alkaline media, and the mechanism of the process was assumed. In the media of high acidity (H-o > -8) the 1,2-dinitroguanidine suffers reversible denitration into nitroguanidine. At lower acidity its conjugate acid or molecular form undergoes hydrolysis yielding nitrourea. Monoanion of 1,2-dinitroguanidine in a weak acid or in an alkali is hydrolyzed into N,N'-dinitrourea. The reaction of 1,2-dinitroguanidine with alkali in alcohol provides its salts, with nitrogen-containing bases form both salts and derivatives of 2-nitroguanidine. The treatment of 1,2-dinitroguanidine with haloalkanes results in its N-alkylated products.