dibenzocycloheptadienylidene | 15306-40-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: dibenzocycloheptadienylidene
• 英文别名: 10,11-Dihydro-dibenzocycloheptenyliden-(5)-radikal
• CAS: 15306-40-8
• 化学式: C₁₅H₁₂
• 分子量: 192.26
• InChiKey: IGDDFRCAYVGHBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对三氟甲基苯乙烯 、 dibenzocycloheptadienylidene 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Carbenadibenzocycloheptane: steady-state and time-resolved spectroscopic laser studies

  摘要：

  DOI：

  10.1021/jo00379a023
• 作为产物：
  描述：

  5-diazo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene 生成 dibenzocycloheptadienylidene
  参考文献：
  名称：

  芳基卡宾与路易斯酸的反应

  摘要：

  在基质分离条件下，研究了三种三重态基态芳基碳烯二苯基卡宾1，芴基2和二苯并环庚二烯基3与路易斯酸H 2 O，ICF 3和BF 3的反应。选择H 2 O作为典型的氢键供体，选择ICF 3作为卤素键供体，选择BF 3作为强路易斯酸。H 2 O与1和2形成单线卡宾氢键合的络合物，但与3形成氢键键合的络合物。较大的单重态-三重态缺口为3可以合理化，这不允许通过氢键将单线态稳定在三线态以下。使用ICF 3时，1和3均会形成卡宾单线态的卤素键合络合物。这表明卤素键比氢键更能稳定单线碳烯。碳2通过形成碘鎓内鎓盐而与1和3反应不同，因此避免了芴基单元的抗芳香族不稳定。与BF 3一起，所有三种卡宾均形成两性离子路易斯酸/碱复合物。

  DOI：

  10.1002/chem.201803695

文献信息

• Activation of Molecular Hydrogen by Arylcarbenes
  作者：Enrique Mendez‐Vega、Mika Maehara、Akshay Hemant Raut、Joel Mieres‐Perez、Masashi Tsuge、Yuan‐Pern Lee、Wolfram Sander

  DOI：10.1002/chem.201804657

  日期：2018.12.12

  The hydrogenation reactions of diphenylcarbene 1, fluorenylidene 2, and dibenzocycloheptadienylidene 3 were investigated in solid H2 and D2 matrices and in H2‐ and D2‐doped argon matrices at cryogenic temperatures. The reactivity of the carbenes towards H2 increases in the order 1<3<2. Whereas 1 is stable in solid H2, 2 and 3 react fast under the same conditions via quantum chemical tunneling. In D2

  diphenylcarbene的氢化反应1，芴2和dibenzocycloheptadienylidene 3在固体1 H进行了调查2和d 2矩阵和H中2和d - 2点在低温下掺杂氩矩阵。卡宾对H 2的反应性以1 < 3 < 2的顺序增加。而1是稳定的固体。1 H 2，2和3的反应快速通过量子隧穿化学相同的条件下。在D 2中都1和3稳定，而2缓慢反应。根据不同的卡宾稳定能，合理化了三种卡宾的不同反应性。
• Contributions of quantum mechanical tunneling to the rate of benzylic hydrogen atom abstraction reactions of triplet diarylcarbenes in fluid solution
  作者：Myron W. Shaffer、Elisa Leyva、N. Soundararajan、Edith Chang、David H. S. Chang、Vince Capuano、Matthew S. Platz

  DOI：10.1021/j100172a033

  日期：1991.9

  Kinetic isotope effects for the benzylic hydrogen atom abstraction reactions of the triplet states of several diarylcarbenes with toluene-toluene-d8 in fluid solution were determined by measuring the ratio of 1,2-diphenylethane to 1,2-diphenylethane-d7 produced in the reaction. Eight carbenes were studied: dibenzocycloheptadienylidene (DBC); 1-naphthylphenylcarbene (1-NPC), 4-biphenylphenlcarbene (BPC), 2-chlorodiphenylcarbene (C1DPC), 2-trifluoromethyldiphenylcarbene (FDPC), fluorenylidene (F1), anthronylidene (AN), and diphenylcarbene (DPC). For 1-NPC, C1DPC, and FDPC the differential kinetic isotope effects were much larger than predicted by complete loss of all zero point energy in the transition state, indicating that there is a contribution of quantum mechanical tunneling to the H(D) atom transfer process. For DPC, DBC, and PBC the differential kinetic isotope effects were barely consistent with a completely classical atom-transfer reaction. For F1 and AN the data were completely consistent with a purely classical atom-transfer process.
• Transient absorption and two-step laser-induced fluorescence studies of excited states of substituted diphenylcarbenes
  作者：Yoshihisa Fujiwara、Mamoru Sasaki、Yoshifumi Tanimoto、Michiya Ito

  DOI：10.1021/j100339a039

  日期：1989.1
• Triplet-triplet fluorescence and spin polarization: diphenylcarbene and dibenzocycloheptadienylidene
  作者：K. W. Haider、Matthew S. Platz、Alain. Despres、Violaine. Lejeune、Eva. Migirdicyan

  DOI：10.1021/j100364a021

  日期：1990.1
• Arrhenius parameters for hydrogen and chlorine atom abstraction reactions of triplet diphenylcarbene and dibenzocycloheptadienylidene
  作者：Robert L. Barcus、Matthew S. Platz、J. C. Scaiano

  DOI：10.1021/j100287a040

  日期：1987.1