N,N'-bis(p-ethoxybenzylidene)-1,2-diiminoethane | 953426-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N'-bis(p-ethoxybenzylidene)-1,2-diiminoethane
• 英文别名: 1-(4-ethoxyphenyl)-N-[2-[(4-ethoxyphenyl)methylideneamino]ethyl]methanimine
• CAS: 953426-66-9
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: WRSKHICFCMHUOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(p-ethoxybenzylidene)-1,2-diiminoethane 、 zinc(II) chloride 以 not given 为溶剂， 以90%的产率得到dichloro(N,N'-bis(p-ethoxybenzylidene)-1,2-diiminoethane)zinc(II)
  参考文献：
  名称：

  Thermally latent reaction of hemiacetal ester with epoxide controlled by Schiff-base–zinc chloride complexes with tunable catalytic activity

  摘要：

  Schiff-base-zinc chloride complexes (ZnCl2/1(R)) thermal-latently catalyze the reaction of glycidyl phenyl ether (2) and I -propoxyethyl-2ethylhexanate (3) that proceeds at appropriate temperatures for latent curing. This reaction proceeds via the nucleophilic addition of carboxylic acid generated from the thermal dissociation of 3 to'2, which takes place faster than the reaction without (ZnCl2/1(R)). Catalytic activities of (ZnCl2/1(R)), depending on the basicities of the a-diimine ligands controllable by the substituents on the aromatic rings, were evaluated by kinetic parameters; namely the reaction rate constants (k), the activation energies (E-a), and the frequency factors (A). (ZnCl2/1(R)) bearing the electron-withdrawing chlorine group initiates the reaction above 80 degrees C, whereas (ZnCl2/1(OMe)), bearing the electron-donating methoxy group initiates the reaction above 100 degrees C. The E-a values in the reactions with (ZnCl2/1(Cl)) and (ZnCl2/1(OMe)), were estimated to be 52.2 and 177 kJ mol(-1), respectively, which agree with the latencies at ambient temperatures. The A values also differ with the catalysts (6.46 x 10(2) and 2.04 x 10(19) L mol(-1) s(-1) for (ZnCl2/1(Cl)) and (ZnCl2/1(OMe)), respectively). The very high A values for the catalysts with electron-donating groups manifest the very good latencies under ambient conditions, in spite of the high activities at elevated temperatures. The coordination behavior of (ZnCl2/1(R)) was evaluated by H-1 NMR, C-13 NMR, N-15 NMR, and lR spectroscopies to understand the substituent effects. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2007.04.016

文献信息

• Thermally latent reaction of hemiacetal ester with epoxide controlled by Schiff-base–zinc chloride complexes with tunable catalytic activity
  作者：Hiroyuki Komatsu、Bungo Ochiai、Tetsuo Hino、Takeshi Endo

  DOI：10.1016/j.molcata.2007.04.016

  日期：2007.8

  Schiff-base-zinc chloride complexes (ZnCl2/1(R)) thermal-latently catalyze the reaction of glycidyl phenyl ether (2) and I -propoxyethyl-2ethylhexanate (3) that proceeds at appropriate temperatures for latent curing. This reaction proceeds via the nucleophilic addition of carboxylic acid generated from the thermal dissociation of 3 to'2, which takes place faster than the reaction without (ZnCl2/1(R)). Catalytic activities of (ZnCl2/1(R)), depending on the basicities of the a-diimine ligands controllable by the substituents on the aromatic rings, were evaluated by kinetic parameters; namely the reaction rate constants (k), the activation energies (E-a), and the frequency factors (A). (ZnCl2/1(R)) bearing the electron-withdrawing chlorine group initiates the reaction above 80 degrees C, whereas (ZnCl2/1(OMe)), bearing the electron-donating methoxy group initiates the reaction above 100 degrees C. The E-a values in the reactions with (ZnCl2/1(Cl)) and (ZnCl2/1(OMe)), were estimated to be 52.2 and 177 kJ mol(-1), respectively, which agree with the latencies at ambient temperatures. The A values also differ with the catalysts (6.46 x 10(2) and 2.04 x 10(19) L mol(-1) s(-1) for (ZnCl2/1(Cl)) and (ZnCl2/1(OMe)), respectively). The very high A values for the catalysts with electron-donating groups manifest the very good latencies under ambient conditions, in spite of the high activities at elevated temperatures. The coordination behavior of (ZnCl2/1(R)) was evaluated by H-1 NMR, C-13 NMR, N-15 NMR, and lR spectroscopies to understand the substituent effects. (C) 2007 Elsevier B.V. All rights reserved.