β-(2'-pyridyl-amino)crotonyl-2-pyridylamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: β-(2'-pyridyl-amino)crotonyl-2-pyridylamide
• 英文别名: (Z)-N-pyridin-2-yl-3-(pyridin-2-ylamino)but-2-enamide
• 化学式: C₁₄H₁₄N₄O
• 分子量: 254.291
• InChiKey: YLADWIVDKMDRDT-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 乙酰乙酸乙酯 反应 5.0h， 以28%的产率得到β-(2'-pyridyl-amino)crotonyl-2-pyridylamide
  参考文献：
  名称：

  Structural characterization of β-2′-pyridylaminocrotonoyl-2-pyridylamide by ESI-MS, NMR, single crystal X-ray analysis and ab initio methods

  摘要：

  In contradiction with earlier reports H-1, C-13 and N-15 NMR spectra show that beta-2'-pyridylaminocrotonoyl-2-pyridylamide is the only form present in chloroform solution. According to the X-ray data the same tautomer exists also in the crystal state. The studied amide has a dimeric form where the monomer molecules are held together by two intermolecular hydrogen bonds. The NMR spectral data show that there is also an intramolecular hydrogen bond in each monomer subunit. The dilution experiments and variable-temperature H-1 NMR runs show that beta-2'-pyridylaminocrotonoyl-2-pyridylamide tends to form the dimers also in chloroform solution at higher concentrations. The ESI-TOF MS measurements at different concentrations confirm that there is a dimerization process taking place in solution. The calculated energetic effect of dimerization of beta-2'-pyridylaminocrotonoyl-2-pyridylamide in vacuum is equal to -34 kJ/mol (exothermic process). X-ray analysis shows that the molecule in crystalline state is not planar. The ab initio RHF/6-31 G** calculations approximate well the X-ray determined molecular geometry of beta-2'pyridylaminocrotonoyl-2-pyridyl-amide. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(03)00181-9