4-[[3-[(2,4-Dihydroxyphenyl)methylideneamino]-4-methylphenyl]iminomethyl]benzene-1,3-diol | 717824-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-[[3-[(2,4-Dihydroxyphenyl)methylideneamino]-4-methylphenyl]iminomethyl]benzene-1,3-diol
• CAS: 717824-31-2
• 化学式: C₂₁H₁₈N₂O₄
• 分子量: 362.385
• InChiKey: CFGCLZLVOJZMHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-二氨基甲苯 、 2,4-二羟基苯甲醛 以 甲苯 为溶剂， 反应 3.0h， 以65%的产率得到4-[[3-[(2,4-Dihydroxyphenyl)methylideneamino]-4-methylphenyl]iminomethyl]benzene-1,3-diol
  参考文献：
  名称：

  Synthesis, characterization and intramolecular proton transfer of 3,3′-dihydroxy-4,4′-[5-methyl-1,3-phenylenebis(nitrilomethylidyne)]-bis-phenol

  摘要：

  A newly synthesized Schiff base, 3,3'-dihydroxy-4,4'-[5-methyl-1,3-phenylenebis(nitrilomethylidyne)]-bis-phenol, was characterized experimentally. Its geometries optimization, tautomerization, assignment of the IR bands and NMR chemical shifts were calculated by using density functional theory (DFT) method. In addition, the atoms in molecules (AIM) analysis was employed for investigation of its tautomerization. Four possible tautomers of the investigated Schiff base were optimized in both of the gas and solution phases. The Schiff base has no planar structure, but each of the benzene rings is in a separate plane. In the most stable tautomer, the phenolic protons of the two -OH groups are engaged in the intramolecular-hydrogen bond with the azomethine nitrogens. Good consistency between the theoretical and experimental results confirms validity of the optimized geometry. Also, kinetics and mechanism of the intramolecular-proton transfer of the studied Schiff base was demonstrated theoretically. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.05.003