2,4,6-三苯基吡喃硫酸氢盐

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4,6-三苯基吡喃硫酸氢盐
• 英文名称: 2,4,6-triphenylpyrylium hydrogen sulfate
• 英文别名: Hydron;2,4,6-triphenylpyrylium;sulfate；hydron;2,4,6-triphenylpyrylium;sulfate
• 化学式: C₂₃H₁₇O*HO₄S
• 分子量: 406.459
• InChiKey: IPEOZISWOGHJJY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氨基-2,6-二苯基苯酚 、 2,4,6-三苯基吡喃硫酸氢盐 在 sodium hydroxide 、 sodium acetate 作用下， 生成 2,6-二苯基-4-(2,4,6-三苯基吡啶)
  参考文献：
  名称：

  An Improved Synthesis of the Solvatochromic Dye ET-30

  摘要：

  描述了一种改进的合成方法，用于著名染料ET-30，该染料作为溶剂极性的表征标准，采用易于获得的原料。

  DOI：

  10.1055/s-1988-27662
• 作为产物：
  描述：

  反式-查耳酮 、 苯乙酮 以80%的产率得到
  参考文献：
  名称：

  DINCULESCU, A.;BALABAN, A. T., ORG. PREP. AND PROCED. INT., 1984, 16, N 5-6, 407-410

  摘要：

  DOI：

文献信息

• Synthesis and structures of crystalline solvates formed of pyridinium N-phenoxide (Reichardt's-type) betaine dyes and alcohols
  作者：Sandra Kurjatschij、Wilhelm Seichter、Edwin Weber

  DOI：10.1039/b9nj00540d

  日期：——

  Four new betaine dyes of the Reichardt's type featuring two tolyl substituents in different attachment (2–4) or being an analogous 1-naphthyl derivative (5) have been synthesized and described with reference to their negative solvatochromism. The dinaphthyl derivative 5 and also a corresponding intermediate nitrophenol 9d were shown with variable-temperature NMR spectroscopy to form conformational atropisomers in solution. Crystal structures of seven alcoholic solvent complexes including the unsubstituted parent compound (1) and different alcohols [1·EtOH (1 : 1), 1·i-PrOH (1 : 1), 2·MeOH (1 : 2), 3·i-PrOH (1 : 1), 3·n-BuOH (1 : 1), 4·EtOH (1 : 2) and 5·MeOH (1 : 3)] have been studied using X-ray diffraction methods. The betaine dyes exist as genuine zwitterion ground state structures in the solid state with twisted conformation between the phenoxide and pyridinium rings. With the exception of 3a [3·i-PrOH (1 : 1)], the alcohol guests in the complexes are hydrogen bonded to the oxygen atom of the phenoxide units, whereas in the i-PrOH complex of 3, the alcohol forms trimeric clusters without specific interaction with the betaine framework. From the packing modes in the crystals, the solvated betaines may be classified either as co-ordination type inclusion compounds with pocket-like host arrangements [1·EtOH (1 : 1), 1·i-PrOH (1 : 1), 2·MeOH (1 : 2), 3·n-BuOH (1 : 1), 4·EtOH (1 : 2) and 5·MeOH (1 : 3)], or a true clathrate with channel-type topology [3·i-PrOH (1 : 1)].

  我们合成了四种新的赖氏甜菜碱染料，它们具有两个不同连接的甲苯基取代基（2-4）或类似的 1-萘基衍生物（5），并介绍了它们的负溶解色度。变温核磁共振光谱显示，二萘基衍生物 5 和相应的中间体硝基苯酚 9d 在溶液中形成构象异构体。利用 X 射线衍射方法研究了七种醇溶剂复合物的晶体结构，包括未取代的母体化合物（1）和不同的醇[1-EtOH (1 : 1)、1-i-PrOH (1 : 1)、2-MeOH (1 : 2)、3-i-PrOH (1 : 1)、3-n-BuOH (1 : 1)、4-EtOH (1 : 2) 和 5-MeOH (1 : 3)]。甜菜碱染料在固态下以真正的齐聚物基态结构存在，苯氧基环和吡啶鎓环之间呈扭曲构象。除 3a [3-i-PrOH (1 : 1)]外，复合物中的醇客体都与苯氧基单元的氧原子氢键结合，而在 3 的 i-PrOH 复合物中，醇形成了三聚簇，与甜菜碱框架没有特定的相互作用。从晶体中的堆积模式来看，溶解的甜菜碱可分为具有口袋状主排列的配位型包合物[1-EtOH（1:1）、1-i-PrOH（1:1）、2-MeOH（1:2）、3-n-BuOH（1:1）、4-EtOH（1:2）和 5-MeOH（1:3）]，或具有通道型拓扑结构的真正包合物[3-i-PrOH（1:1）]。
• Solvent effect on the thermochromism of new betaine dyes
  作者：Rangaraju Satish Kumar、Jaemyeng Jeong、Naveen Mergu、Wooram Oh、Young-A. Son

  DOI：10.1016/j.dyepig.2016.08.034

  日期：2017.1

  thermochromic effect was observed for the dyes and it was attributed to a combination of conformational changes coupled with the relative permittivity of the respective solvent. The thermochromic properties of the betaines were evaluated by UV–Vis studies, and DFT calculations were conducted to rationalize the dye structures. Finally this is the first attempt of the study of color changes in numerous

  在本研究中，成功​​合成了5种甜菜碱染料BT1，BT2，BT3，BT4和BT5，并通过1 H NMR进行了全面表征，1313 C NMR，ESI-MS，IR和UV-可见光谱。除了BT5，其余的甜菜碱染料都是新合成的。这些染料的可逆热致变色性质是在不同温度，不同溶剂中研究的。对于染料观察到大的热致变色效应，这归因于构象变化与相应溶剂的相对介电常数的组合。通过UV-Vis研究评估了甜菜碱的热变色特性，并进行了DFT计算以使染料结构合理化。最后，这是研究多种溶剂在不同温度下颜色变化的首次尝试。
• Photoinduced Processes within Compact Dyads Based on Triphenylpyridinium-Functionalized Bipyridyl Complexes of Ruthenium(II)
  作者：Philippe P. Lainé、Ilaria Ciofini、Philippe Ochsenbein、Edmond Amouyal、Carlo Adamo、Fethi Bedioui

  DOI：10.1002/chem.200401150

  日期：2005.6.6

  electronic absorption properties and electrochemical behavior of the compounds. The capability of 1-bpy and 2-bpy to undergo PET process was evaluated by carrying out their photophysical study (steady state emission and time-resolved spectroscopy at both 293 and 77 K). The conformational dependence of photoinduced processes within P-(theta (1))-A systems has been established by comparing the photophysical

  作为基于氧化还原级联内远程ET的常规电荷分离功能分子模型的替代方法，已经研究了“紧凑方法”。为此，通常在多元醇体系内的主要氧化还原活性单元之间插入的间隔元件已被去除，从而可以实现增强的刚性，但要以增强组件间电子通信为代价。这里研究的分子组件是P-（θ（1））-A型，其中θ（1）扭转角与光敏剂之间的共轭度（P，Ru（bpy）（3）） }（2+）型）和电子受体（A）。4-N-和4-N-，4'-N-（2,4,6-三苯基吡啶基）-2,2'-联吡啶配体（分别为A（1）-bpy和A（2）-bpy）具有合成了分别与Ru（II），1-bpy和2-bpy的配合物。结合了固态分析（X射线晶体学），溶液研究（（1）H NMR，循环伏安法）和计算结构优化，可以验证θ（1）角在溶液中的1-bpy和2-bpy内接近90度。另外，通过研究化合物的电子吸收性能和电化学行为，已经确认了预期存在的强组分间电子偶联。通过进行
• Experimental and computational studies on the solvatochromism and thermochromism of 4-pyridiniophenolates
  作者：John O. Morley、James Padfield

  DOI：10.1039/b204654g

  日期：2002.10.1

  The observed solvatochromism of the betaine 4-(2,4,6-triphenyl-1-pyridinio)phenolate (2a) in solvents of low and very high relative permittivity has been assessed both experimentally and theoretically using molecular orbital methods. The PM3/COSMO method suggests that there are a number of possible conformations for the betaine involving clockwise or anti-clockwise rotation of the four pendant phenyl groups relative to the central heterocyclic ring. The large thermochromic effect observed for the dye in acetone or tetrahydrofuran on moving from room temperature to −78 °C has been attributed to a combination of conformational changes coupled with an increase in the relative permittivity of the respective solvent. The calculated spectroscopic shifts for the betaine using a multi-electron configuration interaction treatment show similar trends to those found experimentally in aprotic solvents. In solvents with acidic hydrogens, the large hypsochromic shift observed for the betaine in the visible region arises from both a dielectric effect and a hydrogen bonding effect. Stable hydrogen bonded structures are predicted to be formed between either water, chloroform, or acetonitrile and the exocyclic oxygen atom of the betaine. The overall shifts observed in these solvents show a good correlation with those calculated for the postulated solvates using a version of the CNDO/S method.

  利用分子轨道方法，对甜菜碱 4-(2,4,6-三苯基-1-吡啶)苯酚（2a）在低和极高相对介电常数溶剂中的溶解变色现象进行了实验和理论评估。PM3/COSMO 方法表明，甜菜碱有多种可能的构象，其中涉及四个悬垂苯基相对于中心杂环的顺时针或逆时针旋转。在丙酮或四氢呋喃中观察到的染料从室温移至 -78 °C时的巨大热变色效应可归因于构象变化与相应溶剂相对介电常数增加的结合。利用多电子构型相互作用处理方法计算出的甜菜碱光谱偏移显示出与在非沸腾溶剂中实验发现的相似趋势。在具有酸性氢的溶剂中，甜菜碱在可见光区域观察到的大的低色度偏移来自介电效应和氢键效应。根据预测，水、氯仿或乙腈与甜菜碱的外环氧原子之间会形成稳定的氢键结构。在这些溶剂中观察到的总体偏移与使用 CNDO/S 方法计算出的假定溶质的偏移具有良好的相关性。
• N-(hydrophobe aromatic)pyridinium compounds
  申请人：The Dow Chemical Company

  公开号：US04672118A1

  公开（公告）日：1987-06-09

  Corrosion of metal surfaces in contact with an aqueous medium is inhibited by incorporating a N-(hydrophobe aromatic)pyridinium compound such as N-(p-dodecylphenyl)-2,4,6-trimethylpyridinium sulfoacetate into the aqueous medium.

  将与水介质接触的金属表面的腐蚀抑制，通过将N-(疏水芳香基)吡啶化合物，如N-(对十二烷基苯基)-2,4,6-三甲基吡啶磺酸酯，加入到水介质中。