(4-乙酰基苯基)-N,N,N-三甲基甲铵溴化物 | 205450-98-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (4-乙酰基苯基)-N,N,N-三甲基甲铵溴化物
• 英文名称: N-(4-Acetyl)benzyl-N,N,N-trimethylammonium bromide
• 英文别名: (4-acetylphenyl)-N,N,N-trimethylmethanaminium bromide；(4-acetylphenyl)methyl-trimethylazanium;bromide
• CAS: 205450-98-2
• 化学式: Br*C₁₂H₁₈NO
• 分子量: 272.185
• InChiKey: IHVODKCBPBBZSU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-(溴甲基)苯基)乙酮 、 三甲胺 以 乙醚 、 氯仿 为溶剂， 反应 12.0h， 生成 (4-乙酰基苯基)-N,N,N-三甲基甲铵溴化物
  参考文献：
  名称：

  Photoinduced Electron-Transfer Reactions:  Highly Efficient Cleavage of C−N Bonds and Photogeneration of Tertiary Amines

  摘要：

  The photocleavage of tertiary amine from tetraphenylborates complexed, via ammonium ions, to various chromophore electron accepters has been studied by laser-flash photolysis. Electron transfer from the berate anions to acceptor excited states is determined to be the primary photochemical step leading to homolytic C-N bond scission and concomitant formation of the corresponding tertiary amine. This pathway was established by direct observation of p-benzoylbenzyl (7a), p-acetylbenzyl (7b), beta-naphthylmethyl (7c), and 7-methoxycoumarin-4-methyl (7d) after laser-flash photolysis from N-(4-benzoyl)benzyl-N,N,N-tributylammonium tetraphenylborate (1a), N-(4-acetyl)benzyl-N,N,N-trimethylammonium tetraphenylborate (1b) N,N,N-tributyl-N-(2-methylnaphthalene)ammonium tetraphenylborate (1c), and N,N,N-tributyl-N-(4-methyl-7-methoxycoumarin)ammonium tetraphenylborate (1d), respectively. The presence of radicals (7a-7d) was also suggested by the reaction products. Comparison of the rate constants for quenching of the tripler states from excited (1a, 1b) and singlet states from (1c, 1d) reveals the efficiency of C-N bond cleavage. Quenching constants in the range of 10(9)-10(12) M-1 s(-1) were observed. Differences are accounted for in terms of variations in the electron-accepting excited states and structural characteristics of the chromophore accepters.

  DOI：

  10.1021/jp972855c

文献信息

• Photoinduced Electron-Transfer Reactions:  Highly Efficient Cleavage of C−N Bonds and Photogeneration of Tertiary Amines
  作者：Ananda M. Sarker、Yuji Kaneko、Alexander V. Nikolaitchik、D. C. Neckers

  DOI：10.1021/jp972855c

  日期：1998.7.1

  The photocleavage of tertiary amine from tetraphenylborates complexed, via ammonium ions, to various chromophore electron accepters has been studied by laser-flash photolysis. Electron transfer from the berate anions to acceptor excited states is determined to be the primary photochemical step leading to homolytic C-N bond scission and concomitant formation of the corresponding tertiary amine. This pathway was established by direct observation of p-benzoylbenzyl (7a), p-acetylbenzyl (7b), beta-naphthylmethyl (7c), and 7-methoxycoumarin-4-methyl (7d) after laser-flash photolysis from N-(4-benzoyl)benzyl-N,N,N-tributylammonium tetraphenylborate (1a), N-(4-acetyl)benzyl-N,N,N-trimethylammonium tetraphenylborate (1b) N,N,N-tributyl-N-(2-methylnaphthalene)ammonium tetraphenylborate (1c), and N,N,N-tributyl-N-(4-methyl-7-methoxycoumarin)ammonium tetraphenylborate (1d), respectively. The presence of radicals (7a-7d) was also suggested by the reaction products. Comparison of the rate constants for quenching of the tripler states from excited (1a, 1b) and singlet states from (1c, 1d) reveals the efficiency of C-N bond cleavage. Quenching constants in the range of 10(9)-10(12) M-1 s(-1) were observed. Differences are accounted for in terms of variations in the electron-accepting excited states and structural characteristics of the chromophore accepters.