(Z)-N-Methyl-3-(2-pyridyl)propenamide | 139606-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (Z)-N-Methyl-3-(2-pyridyl)propenamide
• 英文别名: (Z)-N-methyl-3-pyridin-2-ylprop-2-enamide
• CAS: 139606-83-0
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: ROIUYGDOHMVDLP-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-Methyl-3-(2-pyridyl)propenamide 以 二氯甲烷 为溶剂， 生成 (E)-N-Methyl-3-(2-pyridyl)propenamide
  参考文献：
  名称：

  分子间和分子内氢键对 3-(2-吡啶基)丙烯酰胺结构和光异构化的影响

  摘要：

  我们在此报告了我们研究分子内和分子间氢键对氢键对异构 N-甲基-3-（2-吡啶基）丙烯酰胺（E-和 Z-）在溶液中的构象和光化学行为的影响的初步结果并且处于固态。

  DOI：

  10.1021/ja00034a066
• 作为产物：
  描述：

  (E)-ethyl 3-(2-pyridyl)-propenoate 在 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (Z)-N-Methyl-3-(2-pyridyl)propenamide
  参考文献：
  名称：

  The Influence of Inter- and Intramolecular Hydrogen Bonding upon the Structure and Photochemistry of 3-(2-Pyridyl)propenamides

  摘要：

  The molecular structures and photochemical behavior of (E)- and (Z)-N-methyl-3-(2-pyridyl)-propenamide have been investigated in the solid state and in solution. While the molecular conformation of the thermodynamically more stable E isomer is independent of phase or solvent, the conformation of the Z isomer is dependent upon its environment, adopting an s-trans intramolecular hydrogen-bonded conformation in chlorocarbon solvents, an s-cis conformation in methyl sulfoxide solution, and an orthogonal intermolecular hydrogen-bonded conformation in the solid state. The electronic structure of these molecules has been investigated using the semiemperical INDO/S-SCF-CI (ZINDO) algorithm. The two lowest energy adsorption bands are attributed to allowed pi --> pi* transitions; however, the existence of lower energy singlet n,pi* states is predicted. Neither isomer undergoes photoisomerization in the solid state. Photoisomerization of the E isomer is efficient in nonpolar solvents but occurs with decreased efficiency in solvents which are good hydrogen bond acceptors. The Z isomer undergoes photoisomerization only in strong hydrogen bond acceptor solvents which disrupt the intramolecular hydrogen bond. Thus, either inter- or intramolecular hydrogen bonding can influence the efficiency of photoisomerization. Similar results are obtained with several related N-substituted 3-(2-pyridyl)propenamides. These results provide the first example fo countrthermodynamic one-way E --> Z photoisomerization based upon intramolecular hydrogen bonding.

  DOI：

  10.1021/jo00088a040

文献信息

• Effects of inter- and intramolecular hydrogen bonding upon the structure and photoisomerization of 3-(2-pyridyl)propenamides
  作者：Frederick D. Lewis、Charlotte L. Stern、Beth A. Yoon

  DOI：10.1021/ja00034a066

  日期：1992.4

  We report here preliminary results of our investigation of the effects of intra and intermolecular hydrogen bonding upon hydrogen bonding upon the conformation and photochemical behavior of the isomeric N-methyl-3-(2-pyridyl)propenamides (E- and Z-) in solution and in the solid state.

  我们在此报告了我们研究分子内和分子间氢键对氢键对异构 N-甲基-3-（2-吡啶基）丙烯酰胺（E-和 Z-）在溶液中的构象和光化学行为的影响的初步结果并且处于固态。
• The Influence of Inter- and Intramolecular Hydrogen Bonding upon the Structure and Photochemistry of 3-(2-Pyridyl)propenamides
  作者：Frederick D. Lewis、Beth A. Yoon

  DOI：10.1021/jo00088a040

  日期：1994.5

  The molecular structures and photochemical behavior of (E)- and (Z)-N-methyl-3-(2-pyridyl)-propenamide have been investigated in the solid state and in solution. While the molecular conformation of the thermodynamically more stable E isomer is independent of phase or solvent, the conformation of the Z isomer is dependent upon its environment, adopting an s-trans intramolecular hydrogen-bonded conformation in chlorocarbon solvents, an s-cis conformation in methyl sulfoxide solution, and an orthogonal intermolecular hydrogen-bonded conformation in the solid state. The electronic structure of these molecules has been investigated using the semiemperical INDO/S-SCF-CI (ZINDO) algorithm. The two lowest energy adsorption bands are attributed to allowed pi --> pi* transitions; however, the existence of lower energy singlet n,pi* states is predicted. Neither isomer undergoes photoisomerization in the solid state. Photoisomerization of the E isomer is efficient in nonpolar solvents but occurs with decreased efficiency in solvents which are good hydrogen bond acceptors. The Z isomer undergoes photoisomerization only in strong hydrogen bond acceptor solvents which disrupt the intramolecular hydrogen bond. Thus, either inter- or intramolecular hydrogen bonding can influence the efficiency of photoisomerization. Similar results are obtained with several related N-substituted 3-(2-pyridyl)propenamides. These results provide the first example fo countrthermodynamic one-way E --> Z photoisomerization based upon intramolecular hydrogen bonding.