9-Benzyl-10-methylacridin-Kation | 52328-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-Benzyl-10-methylacridin-Kation
• 英文别名: 9-Benzyl-N-methylacridinium；9-benzyl-10-methyl-acridinium；Acridinium, 10-methyl-9-(phenylmethyl)-；9-benzyl-10-methylacridin-10-ium
• CAS: 52328-35-5
• 化学式: C₂₁H₁₈N
• 分子量: 284.381
• InChiKey: JTVACKKFNYKBDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-Benzyl-10-methylacridin-Kation 在 水 作用下， 生成 9-Benzyl-10-methyl-9,10-dihydro-acridin-9-ol
  参考文献：
  名称：

  Bunting, John W.; Chew, Vivian S. F.; Abhyankar, Sudhir B., Canadian Journal of Chemistry, 1984, vol. 62, p. 351 - 354

  摘要：

  DOI：
• 作为产物：
  描述：

  9-benzyl-10-methyl-9,10-dihydroacridine 、 1-benzyl-3-cyanoquinolinium ion 以 乙腈 为溶剂， 生成 9-Benzyl-10-methylacridin-Kation 、 1-苄基-3-氰基-1,4-二氢喹啉
  参考文献：
  名称：

  Steric and Kinetic Isotope Effects in the Deprotonation of Cation Radicals of NADH Synthetic Analogs

  摘要：

  The deprotonation rate constants and kinetic isotope effects of the cation radicals have been determined by combined use of direct electrochemical techniques at micro- and ultramicroelectrodes, redox catalysis, and laser flash photolysis, over a extended series of opposing bases. Significant steric hindrance to deprotonation results from encumbering of the opposing base and of the functional carbon in the cation radical by alkyl groups. Kinetic isotope effects, ranging from 2 to 12 in terms of k(H)/k(D), appear upon substituting H to D at the functional carbon of the cation radical. The modest magnitude of the kinetic isotope effects and the fact that they are insensitive to steric hindrance show that proton (or H-atom) tunneling does not interfere significantly in the deprotonation reaction. All the cation radicals in the methylacridan series are strong acids, with pK(a)'s ranging from 0.8 to 1.7, as determined from thermodynamic cycles involving measured standard potentials and hydride-transfer equilibrium constants.

  DOI：

  10.1021/ja00133a014

文献信息

• Steric and Kinetic Isotope Effects in the Deprotonation of Cation Radicals of NADH Synthetic Analogs
  作者：Agnes Anne、Sylvie Fraoua、Philippe Hapiot、Jacques Moiroux、Jean-Michel Saveant

  DOI：10.1021/ja00133a014

  日期：1995.7

  The deprotonation rate constants and kinetic isotope effects of the cation radicals have been determined by combined use of direct electrochemical techniques at micro- and ultramicroelectrodes, redox catalysis, and laser flash photolysis, over a extended series of opposing bases. Significant steric hindrance to deprotonation results from encumbering of the opposing base and of the functional carbon in the cation radical by alkyl groups. Kinetic isotope effects, ranging from 2 to 12 in terms of k(H)/k(D), appear upon substituting H to D at the functional carbon of the cation radical. The modest magnitude of the kinetic isotope effects and the fact that they are insensitive to steric hindrance show that proton (or H-atom) tunneling does not interfere significantly in the deprotonation reaction. All the cation radicals in the methylacridan series are strong acids, with pK(a)'s ranging from 0.8 to 1.7, as determined from thermodynamic cycles involving measured standard potentials and hydride-transfer equilibrium constants.
• Bunting, John W.; Chew, Vivian S. F.; Abhyankar, Sudhir B., Canadian Journal of Chemistry, 1984, vol. 62, p. 351 - 354
  作者：Bunting, John W.、Chew, Vivian S. F.、Abhyankar, Sudhir B.、Goda, Yukiko

  DOI：——

  日期：——