phenothiazine neutral radical | 76069-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: phenothiazine neutral radical
• 英文别名: phenothiazinyl radical；phenothiazine radical；\；phenothiazin-10-yl；Phenothiazin-Kation-Radikal；Phenothiazinyl-Radikal
• CAS: 76069-04-0
• 化学式: C₁₂H₈NS
• 分子量: 198.268
• InChiKey: GYHHZMUNWLCUAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  14.1
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  phenothiazine neutral radical 在 氧气 作用下， 生成 Phenothiazin-nitroxid
  参考文献：
  名称：

  二苯胺，吩噻嗪和吩恶嗪的光化学反应的ESR研究

  摘要：

  DOI：

  10.1021/j100403a026
• 作为产物：
  描述：

  吩噻嗪 以 氘代苯 为溶剂， 生成 phenothiazine neutral radical
  参考文献：
  名称：

  酚类脱氢吩噻嗪化反应机理

  摘要：

  在有氧条件下用酚直接捕获氧化吩噻嗪代表了一种独特的交叉脱氢CN键形成反应，操作简单。吩噻嗪与酚的交叉脱氢 N-芳基化机制一直是争论的对象，特别是关于底物氧化的顺序及其潜在的自由基或阳离子性质。了解酚类对氧化吩噻嗪的选择性反应性是本研究的主要目标之一。利用电子顺磁共振光谱、循环伏安法、自由基陷阱实验、动力学同位素效应和溶剂效应详细研究了反应机理。最后，利用密度泛函理论（DFT）和破缺对称开壳单线态DFT方法计算关键反应步骤，揭示酚类氧化吩噻嗪化的独特双自由基机制。

  DOI：

  10.1002/chem.201800730

文献信息

• Bond Dissociation Energies of the N−H Bond and Rate Constants for the Reaction with Alkyl, Alkoxyl, and Peroxyl Radicals of Phenothiazines and Related Compounds
  作者：Marco Lucarini、Pamela Pedrielli、Gian Franco Pedulli、Luca Valgimigli、Didier Gigmes、Paul Tordo

  DOI：10.1021/ja992904u

  日期：1999.12.1

  kinetic investigation on the homolytic reactivity of phenothiazine, phenoxazine, and phenoselenazine, of several substituted phenothiazines, and of related tricyclic aromatic amines are reported. All these compounds give, by hydrogen atom abstraction from the N−H group, persistent aminyl radicals. Equilibration of each of these radicals with the parent amine and a reference compound having an easily abstractable

  报告了对吩噻嗪、吩恶嗪和吩硒嗪、几种取代吩噻嗪和相关三环芳胺的均裂反应性的详细热力学和动力学研究的结果。所有这些化合物通过从 NH 基团中提取氢原子，产生持久的氨基自由基。这些自由基中的每一个与母体胺和具有易于提取的氢的参考化合物的平衡使我们能够通过使用 EPR 光谱法确定胺的 NH 键解离能 (BDE)。它们的特点是 BDE 值低（在某些情况下低于 α-生育酚的 O-H 键强度，即 78.3 kcal/mol），因此是非常好的氢原子转移试剂。为了检查三环胺作为抗氧化剂和聚合抑制剂的效率，
• Acid properties of short-lived radicals and their appearance in photoinduced hydrogen atom transfer
  作者：K. B. Petrushenko、A. I. Vokin、V. K. Turchaninov、S. E. Korostova

  DOI：10.1007/bf00962652

  日期：1988.1
• Kemp, Terence J.; Moore, Peter; Quick, Geoffrey R., Journal of the Chemical Society. Perkin transactions II, 1980, p. 291 - 295
  作者：Kemp, Terence J.、Moore, Peter、Quick, Geoffrey R.

  DOI：——

  日期：——
• Two-Laser Photochemistry of Phenothiazine in Solution: Ionization and Bond Cleavage from Upper States
  作者：Glenn A. Smith、W. Grant McGimpsey

  DOI：10.1021/j100062a031

  日期：1994.3

  The one (308 nm)- and two (308 plus 480 nm)-laser photochemistry of phenothiazine in nitrogen-saturated acetonitrile and cyclohexane was investigated. The lowest excited triplet state (T(l)) of phenothiazine was efficiently generated following 308-nm excitation in both acetonitrile and cyclohexane. In cyclohexane, generation of the phenothiazine neutral radical via homolytic N-H bond cleavage from S1 accompanied intersystem crossing. In acetonitrile, photoionization via the singlet manifold yielding the cation radical competes with intersystem crossing and homolytic bond cleavage. An additional route to the neutral radical in acetonitrile is deprotonation of the cation radical. Generation of upper triplet states (T(n)) by 480-nm excitation of T(l) resulted in permanent bleaching of the T-T absorption in both solvents. The triplet bleaching quantum yield was 0.120 in cyclohexane, but only 0.004 in acetonitrile, indicating that relaxation from T(n) to T(l) is more efficient in acetonitrile. Enhanced neutral radical production in cyclohexane and enhanced production of the neutral and cation radicals in acetonitrile were observed concurrently with T(l) depletion. In cyclohexane, the chemical efficiency of two-laser radical production was 0.90, indicating that the majority of T(n) states that do not relax to T(l) undergo bond cleavage. In acetonitrile, neutral and cation radical chemical efficiencies were 0.53 and 0.45, respectively. Thus, bond cleavage and ionization from T(n) are competitive.
• MORKOVNIK, A. S.;DOBAEVA, N. M.;OXLOBYSTIN, O. YU., XIMIYA GETEROTSIKL. SOEDIN., 1981, N 9, 1214-1216
  作者：MORKOVNIK, A. S.、DOBAEVA, N. M.、OXLOBYSTIN, O. YU.

  DOI：——

  日期：——