2,2,3,3-tetracyanocyclopropane-1-carboxylic acid | 716373-14-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2,3,3-tetracyanocyclopropane-1-carboxylic acid
• 英文别名: 2,2,3,3,-tetracyanocyclopropanecarboxylic acid；2,2,3,3-tetracyanocyclopropanecarboxylic acid
• CAS: 716373-14-7
• 化学式: C₈H₂N₄O₂
• 分子量: 186.129
• InChiKey: VNZDJJLUSIUYOG-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C (decomp)
• 沸点：
  717.2±60.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,3,3-tetracyanocyclopropane-1-carboxylic acid 在 calcium iodide 作用下， 以 水 、 异丙醇 为溶剂， 以45%的产率得到calcium 3-cyano-4-dicyanomethylidene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate
  参考文献：
  名称：

  Reaction of 2,2,3,3-Tetracyanocyclopropanecarboxylic Acid with Iodides. Synthesis of 3-Cyano-4-dicyanomethylidene-5-oxo-4,5-dihydro-1H-pyrrol-2-olates

  摘要：

  2,2,3,3-四氰基环丙烷羧酸与钾、钠、钙、锶、钡、铵、N-甲基吡啶、N-甲基喹啉、N,N-二甲基-1,4-二氮杂双环[2.2.2]八烷-1,4-二阳离子以及N,N-二甲苯基碘化物的反应，生成相应的3-氰基-4-二氰基甲基-5-氧-4,5-二氢-1H-吡咯-2-烯酸盐。

  DOI：

  10.1007/s11178-005-0198-7
• 作为产物：
  描述：

  5-溴-2,2-二甲基-1,3-二噁烷-4,6-二酮 、 四氰基乙烯 以 1,4-二氧六环 、 水 为溶剂， 以35%的产率得到2,2,3,3-tetracyanocyclopropane-1-carboxylic acid
  参考文献：
  名称：

  Synthesis of 6,6-dialkyl-4,8-dioxo-5,7-dioxaspiro[2.5]octane-1,1,2,2- tetracarbonitriles and 2,2,3,3-tetracyanocyclopropanecarboxylic acid

  摘要：

  DOI：

  10.1007/s11178-005-0027-z

文献信息

• Hydrolysis of 6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro[2.5]octane-1,1,2,2-tetracarbonitrile
  作者：O. V. Kayukova、I. N. Bardasov、Ya. S. Kayukov、O. V. Ershov、A. V. Eremkin、O. E. Nasakin、V. A. Tafeenko

  DOI：10.1134/s1070428007120184

  日期：2007.12

  Hydrolysis of 6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro[2.5] octane-1,1,2,2-tetracarbonitrile in aqueous dioxane in the presence of hydrogen bromide gave a mixture of 2,2,3,3-tetracyanocyclopropane-1-carboxylic acid and ammonium 3-cyano-4-dicyanomethylidene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate. Hydrolysis of the same compound in the presence of sulfuric acid was accompanied by nitrogen migration and led to the formation of (IR*,2S*,3S*)-1,3-dicyanocyclopropane-1,2-dicarboxamide whose structure was proved by X-ray analysis.
• <i>N</i>-Methylpyridinium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1<i>H</i>-pyrrol-2-olate
  作者：Viktor A. Tafeenko、Aleksander N. Nikolaev、Rene Peschar、Olga V. Kaukova、Henk Schenk、Leonid A. Aslanov

  DOI：10.1107/s0108270104005372

  日期：2004.4.15

  The crystal structure of the title compound, C6H8N+.-C8HN4O2-, is characterized by three independent ion pairs (A, B and C) in the asymmetric unit. Each ion pair consists of an anion and a cation, and the three ion pairs have similar geometric parameters. All the anions are arranged as dianion dimers via two N-H...O hydrogen bonds and the dimers form one-dimensional columns parallel to the b axis as a result of pi-pi interactions. The cations are also stacked, in two different ways: one type of stacking consists of alternating A and B cations, while the other type consists of C cations only. Each dianion dimer stack is surrounded by eight stacks of cations and is not connected directly to other dianion stacks.
• <i>N</i>,<i>N</i>-Dimethylanilinium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1<i>H</i>-pyrrol-2-olate
  作者：Viktor A. Tafeenko、Rene Peschar、Olga V. Kaukova、Henk Schenk、Leonid A. Aslanov

  DOI：10.1107/s0108270103025940

  日期：2004.1.15

  In the title compound, C8H12N+.C8HN4O2-., the anion and cation lie on a crystallographic mirror plane and form planar ribbons via N - H...O [N...O = 2.933 (4) Angstrom, H...O = 2.01 Angstrom and N - H...O = 170degrees] and N - H...N [N...N = 3.016 (5) Angstrom, H...N = 2.15 Angstrom and N - H...N = 169degrees] hydrogen bonds. The ribbons are further linked via weak C - H...O and C - H...N hydrogen bonds. In adjacent planes, anions lie opposite cations; pi-pi interactions ( separation a/2 = 3.520 Angstrom) exist between the anions and the cations, and stacks are formed, running along the a axis. The cations are disordered over two interpenetrating sites, with occupancies of 0.833 (5) and 0.167 (5).
• Poly[[[diaquazinc(II)]-bis(μ₂-3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1<i>H</i>-pyrrol-2-olato-κ²<i>N</i>³:<i>N</i>^3′)] dihydrate]
  作者：Viktor A. Tafeenko、Vladimir V. Chernyshev

  DOI：10.1107/s0108270105013399

  日期：2005.6.15

  The coordination of the 3-cyano-4-dicyanomethylene-5-oxo-4,5- dihydro-1H-pyrrol-2-olate anion to Zn-II, the apical sites of which are occupied by two water molecules, results in the formation of two-dimensional layers of the title coordination polymer, [Zn(C8HN4O2)(2)(H2O)(2)] center dot 2H(2)O}(n), in which the Zn-II cations lie on inversion centres in space group C2/c, with water ligands in the apical sites of octahedral geometry. Hydrogen bonds between coordinated and lattice water molecules, and pi-pi stacking interactions between the anions link adjacent layers into a continuous framework.
• Ammonium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1<i>H</i>-pyrrol-2-olate monohydrate
  作者：Viktor A. Tafeenko、Rene Peschar、Yakov S. Kajukov、Kirill N. Kornilov、Leonid A. Aslanov

  DOI：10.1107/s0108270105009200

  日期：2005.6.15

  Each anion of the title salt, NH4+center dot C8HN4O2-center dot H2O, is linked by two N-H center dot center dot center dot O hydrogen bonds to another anion, thus forming an essentially planar centrosymmetric dimer. The dimers are considered to be molecular building blocks of an anionic wall. The building blocks form infinite ribbons via -C-N center dot center dot center dot N-C- dipole-dipole and pi-pi interactions. Adjacent ribbons are stacked by means of pi-pi interactions, thus forming an anionic wall. Neighbouring walls are connected by (NH4+center dot center dot center dot H2O)(n) chains running along the b axis.