2-cyano-3-(4-cyanophenyl)acrylamide | 6529-26-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-cyano-3-(4-cyanophenyl)acrylamide
• 英文别名: 2-Cyano-3-(4-cyanophenyl)prop-2-enamide
• CAS: 6529-26-6
• 化学式: C₁₁H₇N₃O
• 分子量: 197.196
• InChiKey: IFNKEEUCPMSACO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氰基苯甲醛 、 氰乙酰胺 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-cyano-3-(4-cyanophenyl)acrylamide
  参考文献：
  名称：

  Tuning the Electronic Properties of 2-Cyano-3-phenylacrylamide Derivatives

  摘要：

  We are the first to report the synthesis of a new class of 2-cyanoarylacrylamide (2-CAA) derivatives and observe that the synthesized 2-CAA shows fluorescence properties due to the formation of a dimeric interaction of hydrogen bonds between carbonyl oxygens and amide hydrogens (C=O center dot center dot center dot H-N-C=O center dot center dot center dot H-N center dot center dot center dot); i.e., dimers are linked through dimeric N-H center dot center dot center dot O hydrogen bonds. The single-crystal X-ray structure shows molecules to be hydrogen-bonded dimers, which further form a parallel stacking arrangement, mediated by significant pi-pi interactions. The H-1 NMR and fluorescence spectral studies indicate the coexistence of amide and iminol tautomers in solution, which can be influenced by the nature of the solvent. Further, the excitation-wavelength-dependent fluorescence spectrum and the biexponential fluorescence decay profiles suggest the presence of more than one emitting species; i.e., amide and iminol tautomers coexists in solution. We have also shown that the equilibrium between the two tautomers can be tuned by the judicious choice of electron-donating or -withdrawing substituents.

  DOI：

  10.1021/acs.joc.5b02226

文献信息

• Tuning the Electronic Properties of 2-Cyano-3-phenylacrylamide Derivatives
  作者：Ramachandran Gunasekar、Pichandi Thamaraiselvi、Ravindranath S. Rathore、Kulathu Iyer Sathiyanarayanan、Shanmugam Easwaramoorthi

  DOI：10.1021/acs.joc.5b02226

  日期：2015.12.18

  We are the first to report the synthesis of a new class of 2-cyanoarylacrylamide (2-CAA) derivatives and observe that the synthesized 2-CAA shows fluorescence properties due to the formation of a dimeric interaction of hydrogen bonds between carbonyl oxygens and amide hydrogens (C=O center dot center dot center dot H-N-C=O center dot center dot center dot H-N center dot center dot center dot); i.e., dimers are linked through dimeric N-H center dot center dot center dot O hydrogen bonds. The single-crystal X-ray structure shows molecules to be hydrogen-bonded dimers, which further form a parallel stacking arrangement, mediated by significant pi-pi interactions. The H-1 NMR and fluorescence spectral studies indicate the coexistence of amide and iminol tautomers in solution, which can be influenced by the nature of the solvent. Further, the excitation-wavelength-dependent fluorescence spectrum and the biexponential fluorescence decay profiles suggest the presence of more than one emitting species; i.e., amide and iminol tautomers coexists in solution. We have also shown that the equilibrium between the two tautomers can be tuned by the judicious choice of electron-donating or -withdrawing substituents.