N-(5-nitrosalicylidene)-2-butylamine | 91181-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(5-nitrosalicylidene)-2-butylamine
• 英文别名: 2-(Butan-2-yliminomethyl)-4-nitrophenol
• CAS: 91181-64-5
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: ILHZDAJQPZAZGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  仲丁胺 、 5-硝基水杨醛 以 乙醇 为溶剂， 生成 N-(5-nitrosalicylidene)-2-butylamine
  参考文献：
  名称：

  Tautomeric forms of N-(5-nitrosalicylidene)-2-butylamine: Experimental and theoretical DFT study

  摘要：

  Tautomeric forms of N-(5-nitrosalicylidene)-2-butylamine in various solvents were studied with the IR and NMR (H-1, C-13) spectroscopy. Also computational studies of keto-amine (O center dot center dot center dot HN) and enol-imine (OH center dot center dot center dot N) tautomers of N-(5-nitrosalicylidene)-2-butylamine molecule in the ground state were carried out with the DFT and SCRF theory at B3LYP/6-31G(d,p) level. Experimental data show that the solvent can invert the keto-amino: enol-imine equilibrium. The enol-imine tautomer prevails in non polar CCl4 and weakly polar CDCl3 or CD2Cl2 solvents, while in polar CD3CN solvent the keto-amine form dominates. Theoretical results agree qualitatively with the experimental findings and suggest also that predominance of particular tautomers can be influenced by the aliphatic chain geometry. Theoretical enol-imine model structure corresponding to the vacuum or non polar environment e.g.CCl4 is more stable than the keto-amino counterpart. On the contrary, the keto-amino form is predicted to be more stable than the enol-imine form in aqueous or in CH3CN polar environments. A satisfactory correlation between theoretical H-1 and C-13 shielding constants and experimental H-1 and C-13 chemical shifts becomes an additional argument that the three-dimension structures predicted theoretically should appear in the experimental conditions. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2009.03.007