2-naphthyl radical | 10237-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthyl radical
• 英文别名: β-naphthyl radical；2-Naphthyl-Radikal
• CAS: 10237-50-0
• 化学式: C₁₀H₇
• 分子量: 127.166
• InChiKey: WUTLDUAYWUUYOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• 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

反应信息

• 作为反应物：
  描述：

  2-naphthyl radical 在 1,4-环己二烯 作用下， 生成 萘
  参考文献：
  名称：

  Arylmethyl Radicals from Arylmethoxybromodiazirines

  摘要：

  Photolytic decompositions of 3-arylmethoxy-3-bromodiazirines afford arylmethyl radicals by homolyses of the diazirines' excited states.

  DOI：

  10.1021/ol0400443
• 作为产物：
  描述：

  2-溴萘 以 N-甲基吡咯烷酮 为溶剂， 生成 2-naphthyl radical
  参考文献：
  名称：

  更快的解离：测量速率和计算对芳基卤自由基阴离子屏障的影响

  摘要：

  NMP 中一系列芳基卤化物自由基阴离子 (ArX-: X = Cl, Br) 的碳 - 卤素键解离速率在室温下通过脉冲辐射分解测量，时间分辨率为 10-11 秒。为了获得准确的解离率，需要注意测量和校正竞争性衰变通道。观察到的速率与通过密度泛函 (DFT) 计算在气相中计算的活化能很好地相关。这些速率与通过相同计算方法获得的电子亲和力或解离能没有很好的相关性，尽管文献中报道了这种相关性并且是基于简单模型的预期。计算还发现过渡态结构具有弯曲的碳卤键。通过涉及 phi* 和 sigma* 状态混合的电子效应，弯曲能够大幅降低激活能。计算出这种弯曲引起的混合可以将解离速率提高几个数量级，因此对于理解这些反应至关重要。

  DOI：

  10.1021/ja0389671

文献信息

• A unified reaction network on the formation of five-membered ringed polycyclic aromatic hydrocarbons (PAHs) and their role in ring expansion processes through radical–radical reactions
  作者：Wang Li、Long Zhao、Ralf I. Kaiser

  DOI：10.1039/d2cp05305e

  日期：——

  highlight the importance of methyl-substituted aromatic reactants (biphenyl, naphthalene) which can be converted to the methylene (–CH2˙) motive by hydrogen abstraction or photolysis. Upon reaction with acetylene, methylene-substituted aromatics carrying a hydrogen atom at the ortho position of the ring can be then converted to cyclopentadiene-annulated aromatics thus providing a versatile pathway to five-membered

  利用可调谐真空紫外 (VUV) 光与高分辨率反射飞行时间质谱仪 (Re- TOF-MS)，本研究揭示了携带两个六元环和一个五元环 (C 13 H 10 )的四种不同多环芳烃的分子量增长过程： 3 H -环戊烷[ a ]萘， 1 H -环戊烷[ b ]naphthalene, 1 H -cyclopenta[ a]萘和气相中的芴。973 和 1023 K 的温度模拟燃烧环境中的条件以及富碳恒星和行星状星云的星周包层。这些反应突出了甲基取代的芳族反应物（联苯、萘）的重要性，这些反应物可以通过夺氢或光解转化为亚甲基（–CH 2 ˙）。在与乙炔反应后，在环的邻位带有氢原子的亚甲基取代的芳烃随后可以转化为环戊二烯环芳烃，从而提供了在高温下生成五元环芳烃的通用途径。
• Enemaerke, Rasmus J.; Christensen, Torben B.; Jensen, Henrik, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2001, # 9, p. 1620 - 1630
  作者：Enemaerke, Rasmus J.、Christensen, Torben B.、Jensen, Henrik、Daasbjerg, Kim

  DOI：——

  日期：——
• Two-Laser, Two-Color Photochemistry from Upper Triplet States of 2-Bromonaphthalene and 9-Bromophenanthrene in Benzene
  作者：J. C. Scaiano、B. R. Arnold、W. G. McGimpsey

  DOI：10.1021/j100072a007

  日期：1994.5

  The photochemistry of 2-bromonaphthalene (BrN) and 2-bromophenanthrene (BrP) in benzene was examined using two-laser, two-color techniques. These experiments center on the photochemistry of the strongly absorbing triplet states of these molecules. Triplet photobleaching quantum yields in benzene are 0.12 and 0.15 for BrN and BrP, respectively. It is believed that these yields coincide with C-Br bond cleavage to yield in-cage radical pairs. Their magnitude reflects excited-state partitioning between C-Br bond cleavage and return to the lowest triplet surface. Bromine atoms were detected taking advantage of pi-complex formation in benzene with lambda(max) similar to 540 nm. Less than half of the bleaching events result in the formation of detectable bromine atoms. Geminate radical recombination of the radical pair to regenerate starting material must compete with cage escape, which accounts for the remaining bleaching events.
• Arylmethyl Radicals from Arylmethoxybromodiazirines
  作者：Robert A. Moss、Xiaolin Fu

  DOI：10.1021/ol0400443

  日期：2004.9.1

  Photolytic decompositions of 3-arylmethoxy-3-bromodiazirines afford arylmethyl radicals by homolyses of the diazirines' excited states.
• Faster Dissociation:  Measured Rates and Computed Effects on Barriers in Aryl Halide Radical Anions
  作者：Norihiko Takeda、Pavel V. Poliakov、Andrew R. Cook、John R. Miller

  DOI：10.1021/ja0389671

  日期：2004.4.1

  correlate well with electron affinities or dissociation energies obtained by the same computational methods, although such correlations are reported in the literature and are expected on the basis of simple models. The calculations also found that the transition state structures had bent carbon-halogen bonds. Bending enables large reductions of the activation energies by an electronic effect involving mixing

  NMP 中一系列芳基卤化物自由基阴离子 (ArX-: X = Cl, Br) 的碳 - 卤素键解离速率在室温下通过脉冲辐射分解测量，时间分辨率为 10-11 秒。为了获得准确的解离率，需要注意测量和校正竞争性衰变通道。观察到的速率与通过密度泛函 (DFT) 计算在气相中计算的活化能很好地相关。这些速率与通过相同计算方法获得的电子亲和力或解离能没有很好的相关性，尽管文献中报道了这种相关性并且是基于简单模型的预期。计算还发现过渡态结构具有弯曲的碳卤键。通过涉及 phi* 和 sigma* 状态混合的电子效应，弯曲能够大幅降低激活能。计算出这种弯曲引起的混合可以将解离速率提高几个数量级，因此对于理解这些反应至关重要。