1-methyl-2,6-bis[2-(4-hydroxyphenyl)ethenyl]pyridinium iodide | 1622006-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-2,6-bis[2-(4-hydroxyphenyl)ethenyl]pyridinium iodide
• CAS: 1622006-64-7
• 化学式: C₂₂H₂₀NO₂*I
• 分子量: 457.311
• InChiKey: OANVXNFOJZOFEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44.34
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,6-二甲基吡啶 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 96.0h， 生成 1-methyl-2,6-bis[2-(4-hydroxyphenyl)ethenyl]pyridinium iodide
  参考文献：
  名称：

  Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study

  摘要：

  Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified using the Kamlet-Taft and Catalan approach. The obtained results were rationalized by comparison of electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HE, DFT, MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silica obtained conformational assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative; inferring that the conformational assembly is more complex than was assumed in so far published literature data for this class of compounds. Along with this, the emission spectra of the representative compounds were decomposed by the Multivariate Curve Resolution analysis. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.07.023

文献信息

• Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides
  作者：Milena D. Milošević、Nevena Ž. Prlainović、Miloš Milčić、Vesna Nikolić、Aleksandra Božić、Miljan Bigović、Aleksandar D. Marinković

  DOI：10.1007/s13738-018-1437-5

  日期：2018.11

  quotient of the occupations for the bonding π and anti-bonding π* orbitals of this bond was considered. Good correlations of the selected parameter between double bond lengths with π*/π and 13C chemical shift differences of the bridging group proved them to be adequate descriptor of push–pull character. Synthesized compounds were screened for the antioxidant activity, using 1,1-diphenyl-2-picrylhydrazyl

  在这项工作中，合成了15个对称的1-甲基-2,6-双[2-（取代的苯基）乙烯基]吡啶鎓碘化物。使用IR，1 H和13 C NMR和UV-Vis光谱对它们的结构进行了表征。DFT计算表明s -trans / s -trans构象普遍存在于所有化合物中。使用线性无溶剂化能量关系（LSER），即Kamlet-Taft和Catalán模型，评估了特定和非特定溶剂-溶质相互作用对UV-Vis吸收最大位移的影响。采用单取代基参数方程（SSP）形式的线性自由能关系（LFER）来假设取代基对NMR数据的定量结构-性质关系。TD-DFT结果表明电子跃迁对取代基效应的依赖性。通过与吡啶鎓中心环交叉共轭的2位和6位烯键式双键在13 C化学位移方面的差异分析了这些化合物的推挽特性。同样，键π的职业的商并考虑了该键的反键π *轨道。带有π * / π的双键长度和桥接基团的13 C化学位移差异之间所选参数的良好相关性证明，它们是推挽特性的充分描述。使用1