环戊-1,3-二烯 | 2143-53-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 环戊-1,3-二烯
• 英文名称: cyclopenta-2,4-dienyl
• 英文别名: cyclopentadienyl radical；Cyclopentadienyl
• CAS: 2143-53-5
• 化学式: C₅H₅
• 分子量: 65.0947
• InChiKey: HPYIUKIBUJFXII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  5
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902199090

反应信息

• 作为反应物：
  描述：

  环戊-1,3-二烯 生成 3-乙烯基炔丙基自由基
  参考文献：
  名称：

  Detailed kinetics of cyclopentadiene decomposition studied in a shock tube

  摘要：

  Mixtures of cyclopentadiene diluted with argon were used to investigate its decomposition pattern in a single pulse-shock tube. The temperatures ranged from 1080 to 1550 K and pressures behind the shock were between 1.7-9.6 atm. The cyclopentadiene concentrations ranged from 0.5 to 2%. Gas-chromatographic analysis was used to determine the product distribution. The main products in order of abundance were acetylene, ethylene, methane, allene, propyne, butadiene, propylene, and benzene. The decomposition of cyclopentadiene was simulated with a kinetic scheme containing 44 species and 144 elementary reactions. This was later reduced to only 36 reactions. The ring opening process of the cyclopentadienyl radical was found to be the crucial step in the mechanism. (C) 1997 John Wiley and Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1997)29:7<505::aid-kin4>3.0.co;2-y
• 作为产物：
  描述：

  3-乙烯基炔丙基自由基 生成 环戊-1,3-二烯
  参考文献：
  名称：

  Detailed kinetics of cyclopentadiene decomposition studied in a shock tube

  摘要：

  Mixtures of cyclopentadiene diluted with argon were used to investigate its decomposition pattern in a single pulse-shock tube. The temperatures ranged from 1080 to 1550 K and pressures behind the shock were between 1.7-9.6 atm. The cyclopentadiene concentrations ranged from 0.5 to 2%. Gas-chromatographic analysis was used to determine the product distribution. The main products in order of abundance were acetylene, ethylene, methane, allene, propyne, butadiene, propylene, and benzene. The decomposition of cyclopentadiene was simulated with a kinetic scheme containing 44 species and 144 elementary reactions. This was later reduced to only 36 reactions. The ring opening process of the cyclopentadienyl radical was found to be the crucial step in the mechanism. (C) 1997 John Wiley and Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1997)29:7<505::aid-kin4>3.0.co;2-y

文献信息

• Decomposition of Picolyl Radicals at High Temperature: A Mass Selective Threshold Photoelectron Spectroscopy Study
  作者：Engelbert Reusch、Fabian Holzmeier、Marius Gerlach、Ingo Fischer、Patrick Hemberger

  DOI：10.1002/chem.201903937

  日期：2019.12.20

  The reaction products of the picolyl radicals at high temperature were characterized by mass-selective threshold photoelectron spectroscopy in the gas phase. Aminomethylpyridines were pyrolyzed to initially produce picolyl radicals (m/z=92). At higher temperatures further thermal reaction products are generated in the pyrolysis reactor. All compounds were identified by mass-selected threshold photoelectron

  通过气相质量选择阈值光电子能谱对吡啶甲基自由基在高温下的反应产物进行了表征。氨甲基吡啶热解最初产生吡啶自由基(m/z=92)。在较高温度下，在热解反应器中进一步产生热反应产物。所有化合物均通过质量选择阈值光电子能谱进行鉴定，并对几种迄今尚未探索的反应分子进行了表征。计算中概述了几种解离途径的机制。m/z=91 的光谱，由吡啶甲基氢损失产生，显示四种异构体，两种乙炔基吡咯，其绝热电离能 (IEad ) 为 7.99 eV (2-乙炔基-1H-吡咯) 和 8.12 eV (3-乙炔基-) 1H-吡咯）和两种环戊二烯甲腈，IE 分别为 9.14 eV（环戊-1,3-二烯-1-甲腈）和 9.25 eV（环戊-1,4-二烯-1-甲腈）。第二个连续的氢损失形成氰基环戊二烯基自由基，IE 为 9.07 eV (T0) 和 9.21 eV (S1)。该化合物进一步解离为乙炔和氰基丙炔基(IE=9.35 e
• An ESR study of the photolysis of dicyclopentadienyltitanium dichloride
  作者：Peter B. Brindley、Alwyn G. Davies、Jalal A.-A. Hawari

  DOI：10.1016/0022-328x(83)85055-4

  日期：1983.7

  in the presence of various reagents (oxygen, ethers, pyridine, phosphines, 2-methyl-2-nitropropane, nitrosodurene, biacetyl, and 3,6-di-t-butyl-1,2-benzoquinone). The direct observation of the spectrum of the cyclopentadienyl radical, and the unambiguous resolution of the hyperfine coupling by two chlorine atoms in the spin adduct which the titanium fragment forms with 2-methyl-2-nitropropane suggests

  ESR光谱已用于监测在溶液中或在存在各种试剂（氧气，乙醚，吡啶，膦，2-甲基-2-硝基丙烷，亚硝基磺脲，联乙酰和3）存在下，将二环戊二烯基二氯化钛光解在溶液中时形成的自由基。 ，6-二叔丁基-1,2-苯醌）。直接观察环戊二烯基的光谱，以及钛片段与2-甲基-2-硝基丙烷形成的自旋加合物中两个氯原子对超精细偶联的明确分辨，表明至少在四氢呋喃中，主要众所周知，反应是：
• The photolysis of cyclopentadienyl compounds of tin and mercury. Electron spin resonance spectra and electronic configuration of the cyclopentadienyl, deuteriocyclopentadienyl, and alkylcyclopentadienyl radicals
  作者：Philip J. Barker、Alwyn G. Davies、Man-Wing Tse

  DOI：10.1039/p29800000941

  日期：——

  mechanism. The introduction of alkyl groups breaks the degeneracy of the ψA and ψS molecular orbitals of the π-system by electron release, destabilising the ψS MO, and the e.s.r. spectrum reflects the spin density distribution in the configuration ψA2ψS1. Deuterium has a small but detectable perturbing effect: the ψA MO is destabilised by ca. 100 J mol–1, and thermal mixing of the two energy levels results

  锡（IV）和汞（II）的环戊二烯基衍生物以及汞（II）的烷基环戊二烯基衍生物在溶液中发生光解，以显示合适的自由基RC 5 H 4 ·（es = R，H，D，Me，Et，Pr i或Bu t）。C 5 H 5 ·自由基是平均D 5 h对称的平面π自由基，在有机溴化物存在下，其光谱可能会通过电荷转移机制而变宽。引入烷基的破坏的简并性ψ甲和ψ小号通过电子释放的π系统的分子轨道，动摇ψ小号MO，和ESR光谱反映了配置的自旋密度分布ψ甲2 ψ小号1。氘具有小的但可检测的扰动的效果：ψ甲MO是通过不稳定约 为100J摩尔-1，并在配置的两个能级结果热混合ψ小号1.515 ψ甲1.485。这与共振积分β而不是库仑积分α的振动摄动模型兼容。
• Spectrum of the Cyclopentadienyl Radical
  作者：B. A. THRUSH

  DOI：10.1038/178155a0

  日期：1956.7

  THE great stability of benzene has aroused much interest in the properties of other planar symmetrical cyclic species of formula (CH)n. For even values of n, only cyclo-octatetraene is stable, and is of limited interest owing to puckering of the ring1. The odd series can exist only as radicals or ions and, while several calculations have been made of their resonance energies2–4, only C7H7+ has been observed spectroscopically5, although the acidity of cyclopentadiene6 provides evidence for the stability of the ion C5H5−. Like benzene, both these species have six π-electrons and are expected to have higher resonance energies than the 38 k.cal. predicted for the Cyclopentadienyl radical (C5H5)3,4.

  苯的高度稳定性引起了人们对其他式 (CH)n 的平面对称环状化合物性质的浓厚兴趣。对于 n 的偶数值，只有环辛四烯是稳定的，而且由于环的起皱，它的意义有限1。奇数系列只能以自由基或离子的形式存在，虽然已经对它们的共振能量进行了多次计算2â4，但只有 C7H7+ 在光谱上被观测到5，尽管环戊二烯的酸性6 为离子 C5H5â 的稳定性提供了证据。与苯一样，这两种物质都有六个 Ï 电子，预计它们的共振能量将高于环戊二烯自由基 (C5H5)3,4 预测的 38 k.cal.。
• Investigation of a New Pathway Forming Naphthalene by the Recombination Reaction of Cyclopentadienyl Radicals
  作者：Yoshinori Murakami、Taweesak Saejung、Chikako Ohashi、Nobuyuki Fujii

  DOI：10.1246/cl.2003.1112

  日期：2003.12

  Mechanism of naphthalene (c-C10H8) formation by the recombination of cyclopentadienyl radicals (c-C5H5) was investigated by monitoring the time profiles of H atom behind the reflected shock of trif...

  环戊二烯基 (c-C5H5) 重组形成萘 (c-C10H8) 的机理通过监测三氟乙烯反射冲击后 H 原子的时间分布进行了研究。