cyclopentadienylideneketene | 115252-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclopentadienylideneketene
• 英文别名: Cyclopentadienylidenketene
• CAS: 115252-80-7
• 化学式: C₇H₄O
• 分子量: 104.108
• InChiKey: UDRSOEFPIMVUIW-UHFFFAOYSA-N

物化性质

• 沸点：
  206.2±7.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  496.84 ℃ 、0.1 Pa 条件下， 生成 cyclopentadienylideneketene 、 丙酮
  参考文献：
  名称：

  苯乙炔的光电子光谱研究中的陷阱。环戊二烯基亚烯酮的光电子能谱

  摘要：

  苯乙炔的光电子光谱研究中经常引用的9.24 eV电离能不是由于苯乙炔1而是由苯，C 6 H 6引起的。当存在10.2 eV谱带时，8.9 eV的电离不是由苯乙炔引起的，而是由环戊二烯基亚烯酮12引起的。，或者同时存在7.6 eV谱带时，生成联苯5。环戊二烯基亚烯基烯12是通过四种不同前体的快速真空热解法生成的，可以将红外，质谱和光电子能谱的观察结果联系起来。

  DOI：

  10.1071/ch09641

文献信息

• Mass Spectrometry of Benzyne and Cyclopentadienylideneketene
  作者：Thomas Monsandl、Graham Macfarlane、Robert Flammang、Curt Wentrup

  DOI：10.1071/ch09640

  日期：——

  The formation of cyclopentadienylideneketene 2 and benzyne 1 in flash vacuum thermolysis reactions is investigated by on-line mass spectrometry. Compounds 13, 14, and 15 all afford ketene 2, which decomposes to benzyne and CO in the high-temperature regime. Cyclopentadienylideneketene 2 is stable on the microsecond time-scale of neutralization-reionization experiments. Collisional activation mass spectrometry of m/z 76 from 14, 15, and 5 indicates that the C6H4•+ ions most likely undergo ring opening in the mass spectrometer.

  在线质谱法研究了在闪蒸真空热解反应中形成环戊二烯亚基烯酮 2 和苄 1 的过程。化合物 13、14 和 15 都能生成烯酮 2，烯酮 2 在高温条件下分解为苄和 CO。环戊二烯基亚烯酮 2 在中和-电离实验的微秒时间尺度上是稳定的。来自 14、15 和 5 的 m/z 76 的碰撞活化质谱分析表明，C6H4-+ 离子很可能在质谱仪中发生了开环。
• Characterization of the bisketene photoisomer of benzocyclobutenedione
  作者：Thomas Mosandl、Curt Wentrup

  DOI：10.1021/jo00055a034

  日期：1993.1
• Infrared spectrum of o-benzyne: experiment and theory
  作者：Juliusz G. Radziszewski、B. Andes Hess、Rudolf Zahradnik

  DOI：10.1021/ja00027a007

  日期：1992.1

  The complete set of vibrational frequencies and absolute infrared intensities has been determined for omicron-benzyne and two of its isotopomers: C6D4 and 1,2-(C2C4H4)-C-13. In addition, for the majority of the transitions symmetries were assigned from infrared linear dichroism of the matrix-isolated samples, photooriented with polarized light during several photochemical transformations. Thermal relaxation of the high static pressure created by the initial photofragmentation causes dramatic changes of the fine site structure of each band of omicron-benzyne and results in a single-site infrared absorption spectra. A high-resolution, single-site vibrational spectrum was also obtained independently from laser hole-burning experiments. Band-shape analysis in different inert gas matrices (Ne, Ar, Xe, N2, and CO) greatly facilitates the correlation of isotopomer bands with those of unlabeled omicron-benzyne. The triple bond stretching vibration appears at 1846 cm-1 in a Ne matrix, with an experimental absolute intensity of 2.0 +/- 0.4 km/mol in the unlabeled omicron-benzyne and is polarized along the symmetry axis. It is red-shifted by 2 cm-1 in the perdeutero-omicron-benzyne and by 53 cm-1 in the doubly C-13-labeled compound, in very good agreement with our theoretical prediction (MP2/6-31G**) and previous gas-phase data for omicron-benzyne.
• Polarization Spectroscopy and ab Initio Study of Photooriented Matrix-Isolated Isotopomers of Phthalic Anhydride. Assignment of the Infrared Absorption Spectrum
  作者：Peter R. Biernacki、Piotr Kaszynski、B. Andes Hess、Erik W. Thulstrup、Juliusz G. Radziszewski

  DOI：10.1021/j100017a009

  日期：1995.4

  In this paper we provide an assignment of symmetries for all transitions observed in the infrared spectrum of phthalic anhydride (1a), based on data determined from polarization studies of photooriented 1a. Photoselection, using two electronic transitions in phthalic anhydride 1a, at 34083 and 40650 cm(-1) and of A(1) and B-2 symmetry, respectively, produced two differently oriented uniaxial samples of the anhydride immobilized in neon and other noble-gas matrices. Subsequent polarization measurements in the infrared region, combined with polarized Raman data, allowed a complete determination of transition moment directions for all observed fundamental vibrations. To facilitate definitive spectral assignments, we studied three isotopomers of 1a: 1,2-C-13-labeled phthalic anhydride (1b), the perdeuterated phthalic anhydride (1c), and the alpha-C-13-labeled compound (1d). Absolute infrared absorption intensities were determined for all observed transitions utilizing absolute infrared absorption intensities of CO and CO2, formed in equimolar amounts with o-benzyne (2) in phototransformations of 1, Interpretation of the experimental results and the final assignments were aided by quantum mechanical modeling at the SCF/6-31G** level.
• Aycard, Jean-Pierre; Volanschi, Elena; Hnach, Mohamed, Journal of Chemical Research, Miniprint, 1995, # 9, p. 2068 - 2083
  作者：Aycard, Jean-Pierre、Volanschi, Elena、Hnach, Mohamed、Zineddine, Hamid、N'Guessan, Thomas Yao

  DOI：——

  日期：——