3-(1,3-benzothiazol-2-yl)-1-{(E)-[(2-hydroxy-5-nitrophenyl)imino]methyl}naphthalen-2-ol | 1616735-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(1,3-benzothiazol-2-yl)-1-{(E)-[(2-hydroxy-5-nitrophenyl)imino]methyl}naphthalen-2-ol
• CAS: 1616735-62-6
• 化学式: C₂₄H₁₅N₃O₄S
• 分子量: 441.467
• InChiKey: WBYMGTVBMODCAI-DHRITJCHSA-N

物化性质

• 熔点：
  282-284 °C
• 沸点：
  746.0±70.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108.85
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-(1,3-benzothiazol-2-yl)naphthalen-2-ol 在 溴化铵 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3-(1,3-benzothiazol-2-yl)-1-{(E)-[(2-hydroxy-5-nitrophenyl)imino]methyl}naphthalen-2-ol
  参考文献：
  名称：

  Photophysical properties of Schiff’s bases from 3-(1,3-benzothiazol-2-yl)-2-hydroxy naphthalene-1-carbaldehyde

  摘要：

  A series of novel Schiff's bases have been synthesized from 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde. The presence of hydroxyl group ortho to the benzothiazolyl group as well as the imine linkage lead to the occurrence of excited state intramolecular proton transfer process. The computational strategy was used to study the ESIPT process of the synthesized Schiff's bases, which revealed surprisingly that the keto form predominantly exists in the ground state contradicting the ESIPT process. Density functional theory and time dependent density functional theory have been used to investigate the structural parameters and photophysical properties in different solvents of one of the Schiff's bases. The experimental results correlate well with the computed results. All Schiff's bases show good thermal stability.

  DOI：

  10.1016/j.saa.2014.05.029