tetrafluoro-p-benzosemiquinone radical anion | 42439-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetrafluoro-p-benzosemiquinone radical anion
• 英文别名: tetrafluoro-p-benzoquinone；p-fluoranil radical anion；2.3.5.6-Tetrafluorsemichinon
• CAS: 42439-31-6
• 化学式: C₆F₄O₂
• 分子量: 180.058
• InChiKey: KGUWRGARQOEZNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.13
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  四氰基乙烯 、 tetrafluoro-p-benzosemiquinone radical anion 生成 tetracyanoethylene anion 、 四氟对苯醌
  参考文献：
  名称：

  Electron affinities of di- and tetracyanoethylene and cyanobenzenes based on measurements of gas-phase electron-transfer equilibria

  摘要：

  DOI：

  10.1021/ja00278a014
• 作为产物：
  描述：

  2,3,5,6-四氟对苯二酚 在 水 、 一氧化二氮 作用下， 生成 tetrafluoro-p-benzosemiquinone radical anion
  参考文献：
  名称：

  四氟对苯并半醌阴离子自由基的时间分辨共振拉曼观察

  摘要：

  DOI：

  10.1021/j100239a029

文献信息

• Electron-Transfer Studies of a Peroxide Dianion
  作者：Andrew M. Ullman、Xianru Sun、Daniel J. Graham、Nazario Lopez、Matthew Nava、Rebecca De Las Cuevas、Peter Müller、Elena V. Rybak-Akimova、Christopher C. Cummins、Daniel G. Nocera

  DOI：10.1021/ic500759g

  日期：2014.5.19

  homogeneous ET reaction has been correlated to heterogeneous ET kinetics as measured electrochemically to provide a unified description of ET between the Butler–Volmer and Marcus models. The chemical and electrochemical oxidation kinetics together indicate that the oxidative ET of O22– occurs by an outer-sphere mechanism that exhibits significant nonadiabatic character, suggesting that the highest

  过氧化物的二价阴离子（O 2 2-）可以hexacarboxamide穴状配体的腔体内被分离，[（O 2）⊂mBDCA-5T-H 6 ] 2-，通过氢键稳定，但以其他方式自由质子或金属离子的关联。该特征使得可以化学和电化学方式检查分离的过氧化物的电子转移（ET）动力学。ET [[（O 2）CAmBDCA-5t-H 6 ] 2–阻流光谱法检测了一系列具有七个醌的化合物，还原电位跨度为1V。均相ET反应的动力学与电化学测量的异相ET动力学相关，以提供Butler-Volmer模型和Marcus模型之间ET的统一描述。化学和电化学氧化动力学共同表明，O 2 2–的氧化ET是通过具有显着非绝热特征的外球机理发生的，这表明O 2 2–的最高占据分子轨道穴位中的分子在空间上不受氧化物质的影响。游离二价阴离子过氧化物的ET化学的理解将在金属-空气电池的研究和使用[（O的有用2）⊂mBDCA-5T-H 6
• In Situ Electrochemical EPR Studies of Charge Transfer across the Liquid/Liquid Interface
  作者：Richard D. Webster、Robert A. W. Dryfe、Barry A. Coles、Richard G. Compton

  DOI：10.1021/ac9708147

  日期：1998.2.1

  The in situ measurement of EPR spectra of radical ions generated at the polarized liquid/liquid interface is described in relation to the 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrachloro-p-benzoquinone (TCBQ), and 2,3,5,6-tetrafluoro-p-benzoquinone (TFBQ) radical anions and the tetrathiafulvalene (TTF) radical cation. TCNQ and TTF were chosen as model compounds with which to quantify the performance of a novel liquid/liquid electrochemical EPR cell. The anion radical of TCNQ and the cation radical of TTF in 1,2-dichloroethane (DCE) were produced at the water interface by electron transfer from/to the aqueous-phase ferricyanide/ferrocyanide redox couple by applying a potential difference between the two phases with a four-electrode potentiostat. The EPR signal intensity (at constant magnetic field) of the resultant organic radicals was monitored during potential step experiments which indicated that the EPR data could be modeled in terms of diffusional transport. TCBQ and TFBQ were chosen as compounds to model the electron transfer behavior of biologically important quinones at the oil/water interface. The EPR and voltammetric data obtained from TCBQ/TCBQ-• and TFBQ/TFBQ-• indicated unambiguously that the two semiquinones are stable at the DCE/water interface and do not undergo immediate protonation.

  在极化的液体/液体界面上生成的自由基离子的 EPR 光谱原位测量与 7,7,8,8-四氰基喹啉二甲烷（TCNQ）、2,3,5,6-四氯对苯醌（TCBQ）和 2,3,5,6-四氟对苯醌（TFBQ）自由基阴离子以及四硫富瓦烯（TTF）自由基阳离子有关。TCNQ 和 TTF 被选择为模型化合物，以量化新型液体/液体电化学 EPR 细胞的性能。通过在水界面施加相间电位差，使用四电极电位计从水相的铁氰化物/亚铁氰化物氧化还原对进行电子转移，在 1,2-二氯乙烯（DCE）中生成 TCNQ 的阴离子自由基和 TTF 的阳离子自由基。在潜在阶跃实验中，监测了生成的有机自由基的 EPR 信号强度（在恒定磁场下），这些结果表明 EPR 数据可以用扩散输运模型来描述。TCBQ 和 TFBQ 被选择作为模型化合物，以模拟在油/水界面上生物重要的醌类化合物的电子转移行为。从 TCBQ/TCBQ-• 和 TFBQ/TFBQ-• 获得的 EPR 和伏安数据明确表明，这两种半醌在 DCE/水界面上是稳定的，并且不会立即发生质子化。
• Oxidation Mechanism of NAD Dimer Model Compounds
  作者：Matthias Patz、Yoshihiro Kuwahara、Tomoyoshi Suenobu、Shunichi Fukuzumi

  DOI：10.1246/cl.1997.567

  日期：1997.6

  The oxidation of a dimeric N-benzyldihydronicotinamide with various oxidants such as quinones, triphenyl carbenium ions and a triplet exited tris(bipyridine) ruthenium(II) complex occurs via initial outer-sphere electron transfer followed by fast C–C bond cleavage and second electron transfer. The kinetic studies allow the determination of the oxidation potential of this compound.

  二聚 N-苄基二氢烟酰胺与各种氧化剂（如醌、三苯基碳鎓离子和三重态三（联吡啶）钌 (II) 络合物的氧化）通过初始外球电子转移随后快速 C-C 键断裂和第二电子发生转移。动力学研究可以确定该化合物的氧化电位。
• Entropy changes and electron affinities from gas-phase electron-transfer equilibria: A- + B = A + B-
  作者：Swapan Chowdhury、Thomas Heinis、Eric P. Grimsrud、Paul Kebarle

  DOI：10.1021/j100403a037

  日期：1986.6
• Electron affinity of SF₆ and perfluoromethylcyclohexane. The unusual kinetics of electron transfer reactions A⁻+B=A+B⁻, where A=SF₆ or perfluorinated cyclo‐alkanes
  作者：E. P. Grimsrud、S. Chowdhury、P. Kebarle

  DOI：10.1063/1.449468

  日期：1985.8

  Measurements of the equilibria (1): A−+B=A+B− with a pulsed electron high pressure mass spectrometer lead to ΔG01, ΔH01, and ΔS01. Equilibria involving SF6 as A and perfluoromethylcyclohexane C7F14 provide electron affinities E.A.(SF6)=1.05±0.1 eV and E.A.(C7F14)=1.06±0.15 eV. The kinetics of reactions (1) involving the above two compounds were studied. The rate constants kf for SF−6 +B=SF6+B− were found to increase with exothermicity of the reaction. The temperature dependence for kf was determined. B compounds leading to high exothermicities were associated with kf at the collision limit and essentially no temperature dependence. B of progressively lower electron affinity led to kf below the collision limit and negative temperature dependence, while B with the lowest E.A. but still leading to exothermic reaction produced lowest kf with positive temperature dependence. A model is provided explaining the above behavior. The known large change of geometry between SF−6 and SF6 introduces an internal barrier in the reaction coordinate for the reactions (1) involving SF6.