tetrabutylammonium tetrazolate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tetrabutylammonium tetrazolate
• 英文别名: tetrabutylammonium tetrazolide；Tetrabutylazanium;1,2,3-triaza-4-azanidacyclopenta-2,5-diene
• 化学式: CHN₄*C₁₆H₃₆N
• 分子量: 311.514
• InChiKey: RNYZLTSBLAZEBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  39.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氮唑 、 四丁基氢氧化铵 在 sodium hydroxide 作用下， 以97%的产率得到tetrabutylammonium tetrazolate
  参考文献：
  名称：

  Noncovalent Interactions between Tetrazole and an N,N‘-Diethyl-Substituted Benzamidine

  摘要：

  Amidines have long been known to form strong noncovalent complexes with carboxylates and phosphates. However, their interaction with tetrazoles, which are acidic heterocycles and important bioisosteric replacements for carboxylic acids in medicinal chemistry, has remained unexplored so far. The binding of a tetrazole to an N,N'-diethyl-substituted benzamidine has been studied for the first time by X-ray crystallography, solution NMR methods, and electrospray mass; spectrometry. The amidinium group of model complex 3 was found to prefer an E,Z configuration in the crystal. Benzamidinium and tetrazolate groups alternate along an infinite chain of hydrogen bonds and salt bridges between the amidine-NH groups and the two tetrazole-N atoms next to the ring carbon. In solution, a 1:1 complex was evident from Job's method of continuous variation, and an association constant of 4.0 x 10(3) +/- 1.6 x 10(3) M-1 (in CDCl3/CD3CN, 6:1) could be determined by H-1 NMR dilution experiments. Tetrazolate was not only found to be a weaker ligand than carboxylates but, surprisingly, the binding mode also changed with concentration in neat CDCl3. At low concentrations, the amidine group in complex 3 adapted an E,E configuration as it does in a related carboxylic acid complex 4. With increasing concentration, the E,Z isomer starts to predominate. A free activation enthalpy DeltaG(298)(double dagger) of 64 +/- 1 kJ mol(-1) for the E,E to E,Z isomerization was determined by line shape analysis at different magnetic fields. Binding strength was further probed in a competition experiment between a bisamidine, a carboxylate, and a tetrazolate by electrospray mass spectrometry.

  DOI：

  10.1021/jo005632i
• 作为试剂：
  描述：

  1H-1,2,4-三唑 、 对苯二甲醚 在 tetrabutylammonium tetrazolate 作用下， 以 乙腈 为溶剂， 以40%的产率得到1-(4-甲氧基苯基)-1H-1,2,4-三唑
  参考文献：
  名称：

  配对电合成的亲核芳族取代：甲氧基芳烃与1 H-四唑的反应

  摘要：

  通过配对电合成有效地进行了1 H-四唑，1,2,4-三唑和5-苯基-1 H-四唑阴离子在1,4-二甲氧基苯和1,3,5-三甲氧基苯上的亲核取代反应。使用具有铂阳极和阴极的不分隔电池，并且溶剂是乙腈，其含有杂环阴离子的四丁基铵盐作为电解质。

  DOI：

  10.1016/0040-4039(95)01455-q

文献信息

• In Search of Ionic Liquids Incorporating Azolate Anions
  作者：Alan R. Katritzky、Shailendra Singh、Kostyantyn Kirichenko、Marcin Smiglak、John D. Holbrey、W. Matthew Reichert、Scott K. Spear、Robin D. Rogers

  DOI：10.1002/chem.200500840

  日期：2006.6.2

  with all combinations of the 1-butyl-3-methylimidazolium cation ([C(4)mim](+)) and the heterocyclic azolate anions studied, and with several combinations of tetraethyl or tetrabutylammonium cations and the azolate anions. The [C(4)mim](+) azolates were liquid at room temperature exhibiting large liquid ranges and forming glasses on cooling with glass-transition temperatures in the range of -53 to -82

  28种新型盐，分别与四甲基，四乙基和四丁基铵和1-丁基-3-甲基咪唑鎓阳离子与3,5-二硝基-1,2,4-三重氮酸酯，4-硝基-1,2,3-三重氮酸酯配对分别使用差示扫描量热法（DSC），热重分析（TGA）和单晶制备了2,4-二硝基咪唑盐，4,5-二硝基咪唑盐，4,5-二氰基咪唑盐，4-硝基咪唑盐和四唑酸盐阴离子并进行了表征。 X射线晶体学。阳离子和阴离子的类型和结构对所得盐（包括几种离子液体）的物理化学性质的影响已得到研究和讨论。使用1-丁基-3-甲基咪唑鎓阳离子（[C（4）mim]（+））和杂环偶氮根阴离子的所有组合获得离子液体（定义为mp <100摄氏度）。以及四乙基或四丁基铵阳离子和偶氮根阴离子的几种组合。[C（4）mim]（+）偶氮盐在室温下呈液态，表现出较大的液体范围，并在玻璃化转变温度为-53至-82摄氏度的条件下冷却时形成玻璃（3,5- mp 33℃的二硝基1,1,2,4-
• Noncovalent Interactions between Tetrazole and an <i>N</i>,<i>N</i>‘-Diethyl-Substituted Benzamidine
  作者：Lars Peters、Roland Fröhlich、Alan S. F. Boyd、Arno Kraft

  DOI：10.1021/jo005632i

  日期：2001.5.1

  Amidines have long been known to form strong noncovalent complexes with carboxylates and phosphates. However, their interaction with tetrazoles, which are acidic heterocycles and important bioisosteric replacements for carboxylic acids in medicinal chemistry, has remained unexplored so far. The binding of a tetrazole to an N,N'-diethyl-substituted benzamidine has been studied for the first time by X-ray crystallography, solution NMR methods, and electrospray mass; spectrometry. The amidinium group of model complex 3 was found to prefer an E,Z configuration in the crystal. Benzamidinium and tetrazolate groups alternate along an infinite chain of hydrogen bonds and salt bridges between the amidine-NH groups and the two tetrazole-N atoms next to the ring carbon. In solution, a 1:1 complex was evident from Job's method of continuous variation, and an association constant of 4.0 x 10(3) +/- 1.6 x 10(3) M-1 (in CDCl3/CD3CN, 6:1) could be determined by H-1 NMR dilution experiments. Tetrazolate was not only found to be a weaker ligand than carboxylates but, surprisingly, the binding mode also changed with concentration in neat CDCl3. At low concentrations, the amidine group in complex 3 adapted an E,E configuration as it does in a related carboxylic acid complex 4. With increasing concentration, the E,Z isomer starts to predominate. A free activation enthalpy DeltaG(298)(double dagger) of 64 +/- 1 kJ mol(-1) for the E,E to E,Z isomerization was determined by line shape analysis at different magnetic fields. Binding strength was further probed in a competition experiment between a bisamidine, a carboxylate, and a tetrazolate by electrospray mass spectrometry.