(E)-2-([3,4-dimethylphenylimino]methyl)-3-methoxyphenol | 1608474-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-([3,4-dimethylphenylimino]methyl)-3-methoxyphenol
• CAS: 1608474-76-5
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: PXRJXGHRRKNKRI-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-羟基-6-甲氧基苯甲醛 、 3,4-二甲基苯胺 以 乙醇 为溶剂， 反应 2.0h， 以72%的产率得到(E)-2-([3,4-dimethylphenylimino]methyl)-3-methoxyphenol
  参考文献：
  名称：

  Theoretical and experimental investigation of (E)-2-([3,4-dimethylphenyl)imino]methyl)-3-methoxyphenol: Enol–keto tautomerism, spectroscopic properties, NLO, NBO and NPA analysis

  摘要：

  The molecular structure and spectroscopic properties of (E)-2-([3,4-dimethylphenyl)iminolmethyl)-3methoxyphenol were investigated by X-ray diffraction, FT-IR and UV-vis spectroscopy. The vibrational frequencies calculatedusing DFT/B3LYP/6-31G(d,p) method. Results showed better agreement with the experimental values. The electronic properties was studied and the most prominent transition corresponds to pi ->pi* and pi ->pi*. Two types of intramolecular hydrogen bonds are strong O-H center dot center dot center dot N interactions in enol-imine form and N-H center dot center dot center dot O interactions in keto-amine form are compared by using density functional theory (DFT) method with B3LYP applying 6-31G(d,p) basis set. Both enol-keto tautomers engender six-membered ring due to intramolecular hydrogen bonded interactions.Geometry optimizations in solvent media were performed with the same level of theory by the polarizable continuum model (PCM). The effect of solvents on the tautomeric stability has been investigated. Stability of the molecule arises from hyperconjugative interactions, charge delocalization and intramolecular hydrogen bond has been analyzed using natural bond orbital (NBO) analysis. Molecular electrostatic potential (MEP) of the titled compound was studied for predicting the reactive sites. Mulliken population method and natural population analysis (NPA) have been studied. Population methods and MEP generally provides information regarding the chemical reactivity regions and charge distributions. Additionally, Frontier Molecular Orbitals analysis hasbeen performed from the optimized geometry. These orbitals also related to ionization potential, electron affinity, kinetic stability and hyperpolarizability of the molecule. The molecule exhibited good nonlinear optical (NLO) activity and first order hyperpolarizability. The predicted nonlinear optical properties of the title compound are 18 times greater than ones of urea. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.02.062