N-methyl-6-hydroxyquinolinium iodide | 7270-81-7

• 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: N-methyl-6-hydroxyquinolinium iodide
• 英文别名: Quinolinium, 6-hydroxy-1-methyl-, iodide；1-methylquinolin-1-ium-6-ol;iodide
• CAS: 7270-81-7
• 化学式: C₁₀H₁₀NO*I
• 分子量: 287.1
• InChiKey: QTCUVSUZUHWJIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.63
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  24.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-6-hydroxyquinolinium iodide 在 silver sulfate 作用下， 生成 6-hydroxy-1-methyl-quinolinium; sulfate
  参考文献：
  名称：

  Claus; Howitz, Journal fur praktische Chemie (Leipzig 1954), 1891, vol. <2> 43, p. 522

  摘要：

  DOI：
• 作为产物：
  描述：

  6-羟基喹啉 、 碘甲烷 以 乙腈 为溶剂， 反应 8.0h， 以71%的产率得到N-methyl-6-hydroxyquinolinium iodide
  参考文献：
  名称：

  大行程转换离子液体染料

  摘要：

  我们将质子化形式的染料N-甲基-6-氧喹诺酮[6MQz]作为阳离子掺入离子液体（IL）中，从而合成出IL染料。IL染料N-甲基-6-羟基喹啉双（三氟甲基磺酰基）酰亚胺[6MQc] [NTf 2 ]的特征在于NMR，ATR红外光谱和X射线晶体学。该IL染料的荧光具有Δ的斯托克斯频移大λ = 116 nm和的量子收率φ ˚F乙腈中＝ 0.56。可以在发射光谱中检测与溶剂有关的特征性位移。在其他ILs中，与纯IL染料在467 nm处相比，我们观察到高达28 nm的红移。对于更强的极性溶剂，荧光信号会强烈红移至650 nm，这表明质子在激发态下转移至溶剂分子。这强调了IL结构单元[MQc] +作为光致酸的重要性。

  DOI：

  10.1002/anie.201703832

文献信息

• Excited-state proton-transfer dynamics of 1-methyl-6-hydroxyquinolinium embedded in a solid matrix of poly(2-hydroxyethyl methacrylate)
  作者：Sun-Young Park、Young-Shin Lee、Du-Jeon Jang

  DOI：10.1039/b811180d

  日期：——

  The excited-state intrinsic proton transfer and its geminate recombination, as well as the ground-state equilibria, of 1-methyl-6-hydroxyquinolinium embedded in a solid matrix of poly(2-hydroxyethyl methacrylate) have been studied by measuring time-resolved and steady-state fluorescence spectra along with absorption and excitation spectra. Proton transfer takes place within 3.3 ns to form ion pairs while its back-reaction occurs on the time scale of 3.7 ns. The ion pairs in the rigid alcoholic matrix go through neither diffusion to form free ions nor subsequent electronic rearrangement to form the keto species within their excited-state lifetimes.

  通过测量时间分辨和稳态荧光光谱以及吸收和激发光谱，研究了嵌入聚（2-羟乙基甲基丙烯酸酯）固体基质中的 1-甲基-6-羟基喹啉的激发态本征质子转移及其基态重组，以及基态平衡。质子转移在 3.3 毫微秒内形成离子对，其反向反应在 3.7 毫微秒内发生。刚性酒精基质中的离子对既没有经过扩散形成自由离子，也没有经过随后的电子重排在其激发态生命周期内形成酮体。
• Claus; Howitz, Journal fur praktische Chemie (Leipzig 1954), 1890, vol. <2> 42, p. 232
  作者：Claus、Howitz

  DOI：——

  日期：——
• Some Urethans of Phenolic Quaternary Ammonium Salts
  作者：John H. Gardner、Joseph R. Stevens

  DOI：10.1021/ja01204a047

  日期：1947.12
• Ultrafast Excited-State Deprotonation and Electron Transfer in Hydroxyquinoline Derivatives
  作者：Taeg Gyum Kim、Michael R. Topp

  DOI：10.1021/jp0471655

  日期：2004.11.1

  Excited-state proton transfer, electron transfer, and solvent relaxation processes in N-methyl-6-hydroxyquino-linium (NM6HQ(+)) and N-methyl-7-hydroxyquinolinium (NM7HQ(+)) iodides have been investigated in both acidic and basic solutions. The hydroxyl group behaves like a superacid in the excited state, exhibiting deprotonation times in acidic aqueous solution for NM6HQ(+) and NM7HQ(+) of 2.0 and 4.5 ps, respectively. These rates for intermolecular proton transfer to water molecules are among the fastest reported to date. This high photoacidity correlates with ultrafast intramolecular electron transfer from the hydroxylate (-O-) group to the positively charged pyridinium ring, which can be observed in separate measurements in basic solution, where the ground states exist as the deprotonated neutral forms N-methyl-6-oxyquinolinium (NM6OQ) and N-methyl-7-oxyquinolinium (NM7OQ). The most obvious effect in basic solution is a Stokes shift resulting from solvent relaxation (1.0 ps), driven by the dipole moment change resulting from ultrafast excited-state electron transfer, apparently on the time scale <450 fs. Studies of such coupling between proton transfer and electron transfer offer to provide new insights into the interpretation of other phototautomerization processes.
• DE80768
  申请人：——

  公开号：——

  公开（公告）日：——