1-methyl-4-aminopyridinium triflate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-methyl-4-aminopyridinium triflate
• 英文别名: 1-Methylpyridin-1-ium-4-amine;trifluoromethanesulfonate
• 化学式: CF₃O₃S*C₆H₉N₂
• 分子量: 258.221
• InChiKey: RTURJWDBMCTJJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.14
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 1-methyl-4-aminopyridinium triflate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以60%的产率得到N-(1-methyl-1H-pyridin-4-ylidene)-p-toluenesulfonamide
  参考文献：
  名称：

  Pyridoneimines and Pyridonemethides:  Substituent- and Solvent-Tunable Intramolecular Charge Transfer and Geometric Isomerism

  摘要：

  We have prepared and fully characterized by means of multinuclear NMR and UV-vis spectroscopy a series of pyridoneimines and pyridonemethides in order to show how it is possible to finely tune pi -electron structure properties by properly exploiting substituent and solvent effects. Substituents with different electron-withdrawing capacities were introduced in pyridoneimines 2-4, pyridonemethides 5 and 6, and pyridine sulfonamido derivatives 7-9. The anisochrony of the carbon position of the azinium ring (geometric isomerism) and the exploitation of previously reported C-13 and N-15 shift/pi -electron density relationships allowed the investigation of the extent of intramolecular charge transfer from the donor group to the acceptor pyridinium moiety. By combining different substitutions with the polarity of the surrounding media, we were able to access a whole range of push-pull electron structures in solution, from fully aromatic-zwitterionic to quinoid-neutral, through many possible intermediate situations along the path. Due to the strict correlation between the pi -electron structure of push-pull derivatives and many photonic properties such as nonlinear optical activity, we believe that the achieved results should be valuable for the development of new efficient, tailor-made, heteroaromatic systems with optimized features as advanced organic materials.

  DOI：

  10.1021/jo015937c
• 作为产物：
  描述：

  4-氨基吡啶 、 三氟甲烷磺酸甲酯 以 苯 为溶剂， 反应 15.0h， 生成 1-methyl-4-aminopyridinium triflate
  参考文献：
  名称：

  Pyridoneimines and Pyridonemethides:  Substituent- and Solvent-Tunable Intramolecular Charge Transfer and Geometric Isomerism

  摘要：

  We have prepared and fully characterized by means of multinuclear NMR and UV-vis spectroscopy a series of pyridoneimines and pyridonemethides in order to show how it is possible to finely tune pi -electron structure properties by properly exploiting substituent and solvent effects. Substituents with different electron-withdrawing capacities were introduced in pyridoneimines 2-4, pyridonemethides 5 and 6, and pyridine sulfonamido derivatives 7-9. The anisochrony of the carbon position of the azinium ring (geometric isomerism) and the exploitation of previously reported C-13 and N-15 shift/pi -electron density relationships allowed the investigation of the extent of intramolecular charge transfer from the donor group to the acceptor pyridinium moiety. By combining different substitutions with the polarity of the surrounding media, we were able to access a whole range of push-pull electron structures in solution, from fully aromatic-zwitterionic to quinoid-neutral, through many possible intermediate situations along the path. Due to the strict correlation between the pi -electron structure of push-pull derivatives and many photonic properties such as nonlinear optical activity, we believe that the achieved results should be valuable for the development of new efficient, tailor-made, heteroaromatic systems with optimized features as advanced organic materials.

  DOI：

  10.1021/jo015937c

文献信息

• Pyridoneimines and Pyridonemethides:  Substituent- and Solvent-Tunable Intramolecular Charge Transfer and Geometric Isomerism
  作者：Alessandro Abbotto、Silvia Bradamante、Giorgio A. Pagani

  DOI：10.1021/jo015937c

  日期：2001.12.1

  We have prepared and fully characterized by means of multinuclear NMR and UV-vis spectroscopy a series of pyridoneimines and pyridonemethides in order to show how it is possible to finely tune pi -electron structure properties by properly exploiting substituent and solvent effects. Substituents with different electron-withdrawing capacities were introduced in pyridoneimines 2-4, pyridonemethides 5 and 6, and pyridine sulfonamido derivatives 7-9. The anisochrony of the carbon position of the azinium ring (geometric isomerism) and the exploitation of previously reported C-13 and N-15 shift/pi -electron density relationships allowed the investigation of the extent of intramolecular charge transfer from the donor group to the acceptor pyridinium moiety. By combining different substitutions with the polarity of the surrounding media, we were able to access a whole range of push-pull electron structures in solution, from fully aromatic-zwitterionic to quinoid-neutral, through many possible intermediate situations along the path. Due to the strict correlation between the pi -electron structure of push-pull derivatives and many photonic properties such as nonlinear optical activity, we believe that the achieved results should be valuable for the development of new efficient, tailor-made, heteroaromatic systems with optimized features as advanced organic materials.