1-pyridin-2-yl-N-[4-(pyridin-2-ylmethylideneamino)phenyl]methanimine | 21756-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-pyridin-2-yl-N-[4-(pyridin-2-ylmethylideneamino)phenyl]methanimine
• 英文别名: (6E,7E)-N¹,N⁴-bis((pyridin-2-yl)methylene)benzene-1,4-diamine；(E)-N,N'-bis(pyridin-2-ylmethylene)benzene-1,4-diamine；p-phenylenebis-(picolinealdamine)
• CAS: 21756-21-8
• 化学式: C₁₈H₁₄N₄
• 分子量: 286.336
• InChiKey: KLFMCRJCCXKCAR-JFMUQQRKSA-N

物化性质

• 熔点：
  153-156 °C
• 沸点：
  516.6±35.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.5
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  nickel diacetate 、 1-pyridin-2-yl-N-[4-(pyridin-2-ylmethylideneamino)phenyl]methanimine 以 乙醇 为溶剂， 以75%的产率得到[N,N'-bis(pyridin-2-ylmethylene)benzene-1,4-diamine]tetraaquadinickel(II) acetate
  参考文献：
  名称：

  Schiff base ligands derived from 2-pyridinecarboxaldehyde and its complexes: characterization, thermal, electrochemical, and catalytic activity results

  摘要：

  Two novel Schiff base ligands (E)-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,4-diamine and (E)-N,N'-bis(pyridin-2-ylmethylene)benzene-1,4-diamine and their binuclear Cu(II), Ni(II), and Co(II) complexes have been synthesized from 2-pyridinecarboxaldehyde, 1,4-diaminobenzene, and trans-1,4-diaminocyclohexane. Characterizations of the synthesized compounds were carried out by thermal analysis, analytical and spectroscopic methods. Catalytic activity of the complex compounds showed some low and some high performances towards the oxidation reactions of cyclohexene and styrene, especially higher performances were obtained for the oxidation of styrene. Thermal examination of the title compounds revealed that complex compounds, apart from Cu(II) complex, were more resistant to temperature, which increases their chance to be used as catalysts towards chemical reactions carried out in high temperatures. Electrochemical features of both ligands and complexes have also been explained.

  DOI：

  10.1007/s00706-014-1381-8
• 作为产物：
  描述：

  吡啶-2-甲醛 、 对苯二胺 以 甲醇 、 乙腈 为溶剂， 反应 4.5h， 以85%的产率得到1-pyridin-2-yl-N-[4-(pyridin-2-ylmethylideneamino)phenyl]methanimine
  参考文献：
  名称：

  两种平面刚性吡啶甲醛基双席夫碱在 HCl 溶液中对低碳钢的吸附和缓蚀性能：实验和计算研究

  摘要：

  两个平面刚性双席夫碱，(1E,1'E)-N,N'-(1,4-亚苯基)双(1-(吡啶-2-基)甲亚胺) (PBPM2) 和 (1E,1'E )-N,N'-(1,4-phenylene)bis(1-(pyridin-3-yl)methanimine) (PBPM3) 作为低碳钢在 HCl 溶液中的缓蚀剂进行了研究。实验结果 表明，1.0 mol L -1 HCl的抑制效率与温度呈轻微负相关，而与抑制剂浓度和浸泡时间呈正相关。30℃失重测定得到的PBPM2和PBPM3的最大抑制率分别达到91.88%和92.18%。拟合分析表明，PBPM2和PBPM3符合Langmuir吸附等温线，物理化学吸附机理为 低碳钢的表面。动电位极化测量表明PBPM2和PBPM3是具有阳极特性的混合型抑制剂。接触角和能量色散光谱数据表明，PBPM2和PBPM3在HCl溶液中的作用改变了低碳钢表面的疏水性，从而在金属表面形

  DOI：

  10.1016/j.molliq.2022.118926

文献信息

• Yoshida, Noboru; Ichikawa, Kazuhiko; Shiro, Motoo, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 1, p. 17 - 26
  作者：Yoshida, Noboru、Ichikawa, Kazuhiko、Shiro, Motoo

  DOI：——

  日期：——
• Ethylene oligomerization studies utilizing nickel complexes bearing pyridine-imine ligands
  作者：Liduo Chen、Hongliang Huo、Libo Wang、Qing Kuang、Weiguang Shi、Na Zhang、Zhijun Li、Jun Wang

  DOI：10.1016/j.ica.2019.04.001

  日期：2019.6

  Two pyridine-imine ligands (6E,7E)-N-1,N-4-bis((pyridin-2-yl)methylene)benzene-1,4-diamine (L1) and (6E,13E)-N-1,N-4-bis(1-(pyridin-2-yl)ethylidene)benzene-1,4-diamine (L2) were synthesized in good yields. Reactions with L1 and L2 with Ni salts afforded nickel complexes NiCl2(6E,7E)-N-1,N-4-bis((pyridin-2-yl)methylene)benzene1,4-diamine}NiCl2 (C1) and NiCl2(6E,13E)-N-1,N-4-bis(1-(pyridin-2-yl)ethylidene)benzene-1,4-diamine}NiCl2 (C2). The compounds were characterized through NMR (H-1 NMR and C-13 NMR), IR, UV-Vis, MS and elemental analysis. Upon activation with a co-catalyst, C1 and C2 both displayed good catalytic activity (0.63 x 10(4)-16.66 x 10(4) g/mol Ni h and 0.11 x 10(5)-23.70 x 10(5) g/mol Ni h, respectively) in ethylene oligomerization experiments, the oligomer products followed the classic Schulz-Flory distribution with mostly 1-C-4 = oligomers. The catalytic performance was obviously affected by the reaction parameters including reaction temperature, reaction pressure, Al/Ni molar ratio, reaction time and co-catalyst type. The experimental data suggested that C1 and C2 generally had quite different catalytic performance under the same reaction conditions indicating the catalyst structure had a significant influence on the catalytic performance. The density functional theory (DFT) calculation was utilized to optimize the geometry structure for exploring the relationship between structure and catalytic properties. Combined with a proposed mechanism, reaction intermediates and frontier molecular orbitals were simulated for further studying the intermediates structure and energy variation in ethylene oligomerization process.
• Schiff base ligands derived from 2-pyridinecarboxaldehyde and its complexes: characterization, thermal, electrochemical, and catalytic activity results
  作者：Selma Bal、Sedat S. Bal

  DOI：10.1007/s00706-014-1381-8

  日期：2015.6

  Two novel Schiff base ligands (E)-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,4-diamine and (E)-N,N'-bis(pyridin-2-ylmethylene)benzene-1,4-diamine and their binuclear Cu(II), Ni(II), and Co(II) complexes have been synthesized from 2-pyridinecarboxaldehyde, 1,4-diaminobenzene, and trans-1,4-diaminocyclohexane. Characterizations of the synthesized compounds were carried out by thermal analysis, analytical and spectroscopic methods. Catalytic activity of the complex compounds showed some low and some high performances towards the oxidation reactions of cyclohexene and styrene, especially higher performances were obtained for the oxidation of styrene. Thermal examination of the title compounds revealed that complex compounds, apart from Cu(II) complex, were more resistant to temperature, which increases their chance to be used as catalysts towards chemical reactions carried out in high temperatures. Electrochemical features of both ligands and complexes have also been explained.
• Adsorption and corrosion inhibition performance of two planar rigid pyridinecarboxaldehyde-based double Schiff bases for mild steel in HCl solution: Experimental and computational investigations
  作者：Xiao-Long Li、Bin Xie、Chuan Lai、Jian-Shen Feng、Xiao-Qiang Liu、Luo Chen、Yu-Geng Yang、Run-Wu Ji、Jia-Yu He、Wei Li、Meng-Nan Liu

  DOI：10.1016/j.molliq.2022.118926

  日期：2022.6

  Two planar rigid double Schiff bases, (1E,1′E)-N,N’-(1,4-phenylene)bis(1-(pyridin-2- yl)methanimine) (PBPM2) and (1E,1′E)-N,N’-(1,4-phenylene)bis(1-(pyridin-3-yl)methan- imine) (PBPM3), were investigated as corrosion inhibitors for mild steel in HCl solution. The experimental results presented that the inhibition efficiencies in 1.0 mol L−1 HCl slightly negatively correlate with temperature, while

  两个平面刚性双席夫碱，(1E,1'E)-N,N'-(1,4-亚苯基)双(1-(吡啶-2-基)甲亚胺) (PBPM2) 和 (1E,1'E )-N,N'-(1,4-phenylene)bis(1-(pyridin-3-yl)methanimine) (PBPM3) 作为低碳钢在 HCl 溶液中的缓蚀剂进行了研究。实验结果 表明，1.0 mol L -1 HCl的抑制效率与温度呈轻微负相关，而与抑制剂浓度和浸泡时间呈正相关。30℃失重测定得到的PBPM2和PBPM3的最大抑制率分别达到91.88%和92.18%。拟合分析表明，PBPM2和PBPM3符合Langmuir吸附等温线，物理化学吸附机理为 低碳钢的表面。动电位极化测量表明PBPM2和PBPM3是具有阳极特性的混合型抑制剂。接触角和能量色散光谱数据表明，PBPM2和PBPM3在HCl溶液中的作用改变了低碳钢表面的疏水性，从而在金属表面形