1-<6-(4-tolyl)pyridazn-3-yl>-3-hydroxypyridinium chloride | 144963-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-<6-(4-tolyl)pyridazn-3-yl>-3-hydroxypyridinium chloride
• 英文别名: 1-<6-(4-tolyl)pyridazin-3-yl>-3-hydroxypyridinium chloride；1-[6-(4-methylphenyl)pyridazin-3-yl]pyridin-1-ium-3-ol;chloride
• CAS: 144963-42-8
• 化学式: C₁₆H₁₄N₃O*Cl
• 分子量: 299.76
• InChiKey: YGRUGQKGGFPISL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.56
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<6-(4-tolyl)pyridazn-3-yl>-3-hydroxypyridinium chloride 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (1R,2S,6R,7R)-3,11-Bis-(6-p-tolyl-pyridazin-3-yl)-3,11-diaza-tricyclo[5.3.1.1^2,6]dodeca-4,8-diene-10,12-dione
  参考文献：
  名称：

  Iskander, M. L.; El-Abbady, S. A.; Shalaby, A. A., Polish Journal of Chemistry, 1992, vol. 66, # 6, p. 1015 - 1023

  摘要：

  DOI：

文献信息

• Kinetic Studies of [4n+2]π-Thermal Cyclodimerization of 1-(3-Pyridazinyl)-3-oxidopyridinium Betaines
  作者：Madlene L. Iskander、Samia A. El-Abbady、Alyaa A. Shalaby、Ahmed H. Moustafa

  DOI：10.1135/cccc19921951

  日期：——

  The reactivity of the base induced cyclodimerization of 1-(6-arylpyridazin-3-yl)-3-oxidopyridinium chlorides in a pericyclic process have been investigated kinetically at λ 380 nm. The reaction was found to be second order with respect to the liberated betaine and zero order with respect to the base. On the other hand dedimerization (monomer formation) was found to be first order. It was shown that dimerization is favoured at low temperature, whereas dedimerization process is favoured at relatively high temperature (ca 70 °C). Solvent effects on the reaction rate have been found to follow the order ethanol > chloroform ≈ 1,2-dichloroethane. Complete dissociation was accomplished only in 1,2-dichloroethane at ca 70 °C. The thermodynamic activation parameters have been calculated by a standard method. Thus, ∆G^# has been found to be independent on substituents and solvents. The high negative values of ∆S^# supports the cyclic transition state which is in favour with the concerted mechanism. MO calculations using SCF-PPP approximation method indicated low HOMO-LUMO energy gap of the investigated betaines.

  该研究以光谱学为基础，考察了碱催化的1-(6-芳基吡啶并嗪-3-基)-3-氧化吡啶铵氯化物的环二聚反应动力学，反应在λ 380 nm下进行。发现该反应对于游离的贝塔因子是二阶反应，对于碱是零阶反应。另一方面，反二聚化（单体形成）是一阶反应。研究表明，低温有利于二聚化，而相对较高的温度（约70℃）有利于反二聚化过程。发现溶剂对反应速率的影响遵循乙醇>氯仿≈1,2-二氯乙烷的顺序。只有在约70℃的1,2-二氯乙烷中才能完全解离。采用标准方法计算了热力学活化参数。因此，发现∆G#与取代基和溶剂无关。高负值的∆S#支持有利于协同机理的环状过渡态。使用SCF-PPP逼近方法进行的MO计算表明，研究的贝塔因子具有较低的HOMO-LUMO能隙。