(Z)-1-((3-chlorophenylamino)methylene)naphthalen-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-((3-chlorophenylamino)methylene)naphthalen-2-one
• 英文别名: N-(m-Chlor-phenyl)-2-oxo-1.2-dihydro-naphthyliden-(1)-methylamin；(1Z)-1-[(3-chloroanilino)methylidene]naphthalen-2-one
• 化学式: C₁₇H₁₂ClNO
• 分子量: 281.741
• InChiKey: BNWGBDQQBVFTHU-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-氯苯胺 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 0.5h， 以70.2%的产率得到(Z)-1-((3-chlorophenylamino)methylene)naphthalen-2-one
  参考文献：
  名称：

  Factors determining tautomeric equilibria in Schiff bases

  摘要：

  Schiff bases derived from o-hydroxyaldehydes present keto and enol tautomeric forms: the relative equilibrium between these two tautomers depending on the particular aldehyde the Schiff bases is derived from. Thus benzaldehyde produces a stable enol tautomer, while a naphthaldehyde produces a mixture of keto and enol tautomers. The energy difference between these tautomers is very small (similar to 5 kJ/mol) and therefore close to current precision limits of ab initio and DFT based quantum calculations. NMR spectroscopy results, which allows for the determination of the stable structure when one tautomer is prevalent, can be very difficult to interpret when both tautomers are present. We calculate energy differences between the tautomers and demonstrate that the precision of current DFT calculations is not sufficient to predict the most stable structure. On the other hand, DFT calculations of the NMR chemical shifts (using the CIAO technique) can properly interpret the spectroscopy results allowing the characterization of the experimentally present tautomers and the estimation of the relative abundance of each when both are present. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.10.011

文献信息

• Factors determining tautomeric equilibria in Schiff bases
  作者：Martha Flores-Leonar、Nuria Esturau-Escofet、José M. Méndez-Stivalet、Armando Marı´n-Becerra、Carlos Amador-Bedolla

  DOI：10.1016/j.molstruc.2011.10.011

  日期：2011.12

  Schiff bases derived from o-hydroxyaldehydes present keto and enol tautomeric forms: the relative equilibrium between these two tautomers depending on the particular aldehyde the Schiff bases is derived from. Thus benzaldehyde produces a stable enol tautomer, while a naphthaldehyde produces a mixture of keto and enol tautomers. The energy difference between these tautomers is very small (similar to 5 kJ/mol) and therefore close to current precision limits of ab initio and DFT based quantum calculations. NMR spectroscopy results, which allows for the determination of the stable structure when one tautomer is prevalent, can be very difficult to interpret when both tautomers are present. We calculate energy differences between the tautomers and demonstrate that the precision of current DFT calculations is not sufficient to predict the most stable structure. On the other hand, DFT calculations of the NMR chemical shifts (using the CIAO technique) can properly interpret the spectroscopy results allowing the characterization of the experimentally present tautomers and the estimation of the relative abundance of each when both are present. (C) 2011 Elsevier B.V. All rights reserved.