4-(4'-N,N-dimethylaminostyryl)pyridine N-oxide | 26708-23-6

• 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: 4-(4'-N,N-dimethylaminostyryl)pyridine N-oxide
• 英文别名: 4-(4-N,N-dimethylaminostyryl)pyridine N-oxide；4-[(4'-dimethylamino)styryl]pyridine-1-oxide；4-(4'-dimethylaminostyryl)pyridine N-oxide；4-(4-dimethylaminostyryl)pyridine N-oxide；4-(p-dimethylaminostyryl)pyridine N-oxide；N,N-dimethyl-4-[2-(1-oxidopyridin-1-ium-4-yl)ethenyl]aniline
• CAS: 26708-23-6
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: ZNBFFDGZGHFAOU-UHFFFAOYSA-N

物化性质

• 熔点：
  256-257 °C
• 沸点：
  473.4±24.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  zinc tetraphenylporphyrin 、 4-(4'-N,N-dimethylaminostyryl)pyridine N-oxide 以 丙酮 为溶剂， 生成 zinc(II) tetraphenylporphyrin*(4-(4-dimethylaminostyryl)pyridine N-oxide)
  参考文献：
  名称：

  杂环N-氧化物与Zn（II）四苯基卟啉配合物的热氧化破坏

  摘要：

  应用热重分析，差示热分析和差示扫描量热法研究了杂环N-氧化物与四苯基锌卟啉锌的分子配合物。已计算出单个化合物及其分子配合物的热氧化破坏过程的动力学特征。所得结果表明ZnTPhP与杂芳族N-氧化物的复合形成导致金属卟啉和配体的热稳定性增加。已经显示ZnTPhP与杂芳族N-氧化物的分子复合物的稳定性取决于配位体的碱性。

  DOI：

  10.1007/s10973-007-8444-6
• 作为产物：
  描述：

  4-(二甲胺基丙基)吡啶 、 1-acetyloxy-4-(4-dimethylaminostyryl)pyridinium tetraphenylborate 以 乙腈 为溶剂， 生成 1-acetoxy-4-(dimethylamino)pyridinium tetraphenylborate 、 4-(4'-N,N-dimethylaminostyryl)pyridine N-oxide
  参考文献：
  名称：

  Equilibrium of acyl transfer between pyridine N-oxides and their acylonium salts

  摘要：

  TransFer of' acyl groups from N-acyloxypyridinium salts to pyridine N-oxides in acetonitrile was studied. The equilibrium constants of' acyl exchange were determined. These quantities vary in the range coverino ei,,ht orders of magnituJe, depending on the structure of the reavents. and are independent of' the z' c C C structure ol'the acyl group.

  DOI：

  10.1134/s1070363208060248

文献信息

• Rate and Equilibrium Constants of Benzoyl Group Transfer between Pyridine N-Oxides
  作者：V. I. Rybachenko、G. Schroeder、K. Yu. Chotii、B. Lenska、A. N. Red’ko、V. V. Kovalenko

  DOI：10.1007/s11178-005-0244-5

  日期：2005.5

  Kinetic characteristics of 19 transfer reactions of benzoyl group from N-benzoyloxypyridinium salts to pyridine N-oxides and 4-dimethylaminopyridine were studied in acetonitrile by the stopped-flow method. The rate of an identical reaction for 4-methoxypyridine was measured by dynamic NMR spectroscopy. For 5 other identical reactions the rates were estimated from Bronsted correlations. Equilibrium constants were estimated with the use of UV spectrophotometry (6), IR spectroscopy (2), from kinetic data (K ij = k ij /k ji ) (2), and in one case as logK i−j = logK i−x − logK j−x . The second order rate constants (k ij ) varied in the range 102–105 l mol−1 s−1, the equilibrium constants (K ij ) in the range 102–10−2; the activation parameters (ΔH ≠) were within 15–50 kJ mol−1, (−ΔS ≠) −20–110 J mol−1 K−1. The reactions under study occur in a single stage following the concerted SN2 mechanism through an early associative transition state. The benzoyl groups exchange rate and equilibrium are well described by simplified Marcus equation (omitting the quadratic term).

  在乙腈中采用停流法研究了苯甲酰基从 N-苯甲酰氧基吡啶鎓盐转移到吡啶 N-氧化物和 4-二甲氨基吡啶的 19 个转移反应的动力学特征。通过动态核磁共振光谱法测量了 4-甲氧基吡啶的相同反应速率。其他 5 个相同反应的速率是通过布朗斯梯相关性估算的。平衡常数是通过紫外分光光度法（6）、红外光谱法（2）、动力学数据（K ij = k ij /k ji ）（2）以及 logK i-j = logK i-x - logK j-x 估算得出的。二阶速率常数（k ij ）的变化范围为 102-105 l mol-1 s-1，平衡常数（K ij ）的变化范围为 102-10-2；活化参数（ΔH ≠）的变化范围为 15-50 kJ mol-1，（-ΔS ≠）的变化范围为 -20-110 J mol-1 K-1。所研究的反应是按照协同 SN2 机制通过早期缔合过渡态在一个阶段内发生的。苯甲酰基的交换速率和平衡可以用简化的马库斯方程（省略二次项）很好地描述。
• Extra Coordination of Zn-Tetraphenylporphine with Pyridine, Quinoline, and Acridine N-Oxides
  作者：V. P. Andreev、Ya. P. Nizhnik、D. G. Bezruchko、A. K. Morozov

  DOI：10.1007/s11176-005-0416-6

  日期：2005.8

  The log K values of zinc tetraphenylporphine (Zn-TPhP) complexes with pyridine, quinoline, and acridine N -oxides and with their nonoxidized analogs, as well as the positions of absorption maxima of the complexes with respect to Zn-TPhP linearly depend on the \(pK_BH^ + }\) of the ligands in water (methanol, acetonitrile, nitromethane, and acetone) and on Hammett σ constants in the absence of steric

  四苯基卟啉锌（Zn-TPhP）与吡啶，喹啉和a啶 N- 氧化物及其非氧化类似物的log K 值 以及该复合物相对于Zn-TPhP的最大吸收位置线性取决于水中的配体（甲醇，乙腈，硝基甲烷和丙酮）的\（pK_ BH ^ +} \）和在没有空间位阻效应的情况下的Hammettσ常数。
• Complexing Ability of Heterocyclic N-Oxides Toward Proton Donor Compounds
  作者：N. Sh. Lebedeva、Yu. A. Gubarev、E. S. Yurina、S. S. Guseinov、A. I. V’yugin、V. P. Andreev

  DOI：10.1134/s1070363219070101

  日期：2019.7

  interaction of styryl derivatives of pyridine N-oxides with proton donors in various solvents was studied. UV-Vis spectroscopy and thermogravimetric analysis were applied to determine the spectral and thermo-chemical characteristics of the resulting molecular complexes. The dependences of the thermodynamic parameters of the complexes on the N-oxide structure and on the solvating medium were established

  研究了吡啶N-氧化物的苯乙烯基衍生物与质子供体在各种溶剂中的相互作用。紫外可见光谱和热重分析法用于确定所得分子复合物的光谱和热化学特征。建立了配合物的热力学参数对N-氧化物结构和溶剂化介质的依赖性。DSC方法用于确定N氧化物及其与质子供体的复合物的去溶剂化和熔融过程的温度和焓特征。
• ——
  作者：V. I. Rybachenko、G. Schroeder、K. Yu. Chotii、E. V. Titov、V. V. Kovalenko、B. Leska、L. V. Grebenyuk

  DOI：10.1023/a:1013919523997

  日期：——

  Forty-three (including eight identical) reactions of acetyl transfer from N-acetyloxypyridinium salts to pyridine N-oxides in acetonitrile solutions were studied. The rate constants k(2) vary in the range 10(7)- 10(-1) 1 mol(-1) s(-1); the equilibrium constants K, in the range 10(7)-10(-7); the activation enthalpy DeltaH(not equal), in the range 17-30 kJ mol(-1); the activation entropy -DeltaS(not equal), in the range 60-85 J mol(-1) K-1; and the heat of reaction -DeltaH(0), within +/-50 kJ mol(-1). All reactions occur in a single stage by the concerted SN2 mechanism with a low degree of bond cleavage in the transition state. The rate and equilibrium of the acetyl exchange are satisfactorily described by the Bronsted equation. The quality of predicting the reactivity is substantially improved by introducing into the correlation equation a second parameter, the rates of identical reactions.
• ——
  作者：V. I. Rybachenko、K. Yu. Chotii、V. V. Kovalenko、H. Schroeder

  DOI：10.1023/a:1012377922986

  日期：——

  The equilibrium constants or acetyl transfer between O-acetylonium salts of a series of pyridine N-oxides and 4-(4-dimethylaminostyryl)pyridine N-oxide in acetonitrile and methylene chloride were determined. The equilibrium constants correlate with the acid-base characteristics of the N-oxides and with the heats of reactions calculated quantum-chemically.