cyanocarbene | 129066-39-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cyanocarbene
• 英文别名: Cyancarben；Ethenylideneazanide
• CAS: 129066-39-3
• 化学式: C₂HN
• 分子量: 39.0366
• InChiKey: SZICEGNEOSKVLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  3
• 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：
  1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二溴乙腈 以 various solvent(s) 为溶剂， 生成 cyanocarbene
  参考文献：
  名称：

  Quasi-linearity in HCCN: effects of the v2 fundamental

  摘要：

  The high resolution infrared spectrum of the quasi-linear molecule HCCN in the region of its nu(2) CCN antisymmetric stretching fundamental has been observed. Six separate vibrational bands have been positively identified and rotationally analyzed. The lower states of these transitions belong to the ground state and the first and second excited states of the HCC bending mode (nu(5) in linear molecule notation), nu(5)(+/-1) and 2 nu(5)(+/-2). Multiple occurrences of transitions originating from each of these lower levels combined with the presence of partially resolved fine structure splitting in some bands and its absence in others suggest a strong coupling of the nu(2) mode with otherwise ''dark'' vibrational states. Fermi resonance between nu(2) and a combination level, such as nu(3) + (nu(4) + nu(5))(0+), provides such an intensity borrowing mechanism.

  DOI：

  10.1016/0022-2860(94)08512-g

文献信息

• The Photochemical and Thermal Decomposition of Azidoacetylene in the Gas Phase, Solid Matrix, and Solutions
  作者：Xiaoqing Zeng、Helmut Beckers、Jennifer Seifert、Klaus Banert

  DOI：10.1002/ejoc.201402153

  日期：2014.7

  Decomposition of the extremely explosive and unstable parent compound of 1-azidoalkynes, HCCN3 (azidoacetylene), was studied in the gas phase, solid argon matrix, and solutions. In the gas phase, this azide decomposes quickly at room temperature with a half-life time (t1/2) of 20 min at an initial pressure (p0) of 0.8 mbar. The decay (p0 = 1.0 mbar) is significantly increased in an atmosphere of O2

  在气相、固体氩基质和溶液中研究了极易爆炸且不稳定的 1-叠氮炔母体化合物 HCCN3（叠氮乙炔）的分解。在气相中，这种叠氮化物在室温下快速分解，在 0.8 毫巴的初始压力 (p0) 下，半衰期 (t1/2) 为 20 分钟。衰变 (p0 = 1.0 mbar) 在 O2 气氛中显着增加，t1/2 为 3 分钟，其中 HC(O)CN 被确定为氰卡宾中间体 HCCN 的捕集产物。在溶液中的叠氮化物分解过程中也发现了这种卡宾被溶剂分子（CH2Cl2 和 CHCl3）捕获的产物，而与溴溶液形成二溴乙腈的反应被解释为是通过炔烃本身的亲核攻击发生的。
• The Simplest, Isolable, Alkynyl Isocyanate HC≡CNCO: Synthesis and Characterization
  作者：Yuanyuan Qin、Bo Lu、Guntram Rauhut、Manfred Hagedorn、Klaus Banert、Chao Song、Xianxu Chu、Lina Wang、Xiaoqing Zeng

  DOI：10.1002/anie.201911102

  日期：2019.11.25

  (2 mbar, 300 K) with a melting point of -79.5 °C and vaporization enthalpy (ΔHvap ) of 23.1(1) kJ mol-1 . Apart from the IR (gas, solid, and matrix), 1 H and 13 C NMR, and UV/Vis spectroscopic characterization, its photoisomerization with a acylnitrene HC≡CC(O)N and cyanoketene NCC(H)CO has been observed.

  炔基异氰酸酯已被假定为合成化学中的高反应性中间体。本文中，首次分离出母体分子HC≡CNCO。与先前报道的室温下短寿命（约15 s）形成鲜明对比，我们发现HC≡CNCO在气相（2 mbar，300 K）下的寿命为55 h，熔点为-79.5° C和23.1（1）kJ mol-1的汽化焓（ΔHvap）。除了IR（气体，固体和基质），1 H和13 C NMR以及UV / Vis光谱表征外，还观察到它是通过酰基亚硝基HC≡CC（O）N和氰基烯NCC（H）CO进行光异构化的。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: C: MVol.D1, 11, page 106 - 112
  作者：

  DOI：——

  日期：——
• Merer, A. J.; Travis, D. N., Canadian Journal of Physics, 1965, vol. 43, p. 1795 - 1830
  作者：Merer, A. J.、Travis, D. N.

  DOI：——

  日期：——
• Quasi-linearity in HCCN: effects of the v2 fundamental
  作者：C.E. Miller、W.C. Eckhoff、R.F. Curl

  DOI：10.1016/0022-2860(94)08512-g

  日期：1995.6

  The high resolution infrared spectrum of the quasi-linear molecule HCCN in the region of its nu(2) CCN antisymmetric stretching fundamental has been observed. Six separate vibrational bands have been positively identified and rotationally analyzed. The lower states of these transitions belong to the ground state and the first and second excited states of the HCC bending mode (nu(5) in linear molecule notation), nu(5)(+/-1) and 2 nu(5)(+/-2). Multiple occurrences of transitions originating from each of these lower levels combined with the presence of partially resolved fine structure splitting in some bands and its absence in others suggest a strong coupling of the nu(2) mode with otherwise ''dark'' vibrational states. Fermi resonance between nu(2) and a combination level, such as nu(3) + (nu(4) + nu(5))(0+), provides such an intensity borrowing mechanism.