N-(6-acetamidopyridin-2-yl)pivalamide | 1257227-13-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(6-acetamidopyridin-2-yl)pivalamide
• 英文别名: N-(6-acetamidopyridin-2-yl)-2,2-dimethylpropanamide
• CAS: 1257227-13-6
• 化学式: C₁₂H₁₇N₃O₂
• 分子量: 235.286
• InChiKey: VULLXLQBONMILM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二氨基吡啶 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(6-acetamidopyridin-2-yl)pivalamide
  参考文献：
  名称：

  Understanding the Effects of Preorganization, Rigidity, and Steric Interactions in Synthetic Barbiturate Receptors

  摘要：

  Synthetic barbiturate receptors have been utilized for many applications due to their high binding affinities for complementary guests. Although interest in this class of receptors spans from supramolecular to materials chemistry, the effects of receptor steric bulk and preorganization on guest binding affinity has not been studied systematically. To investigate the roles that steric bulk and preorganization play in guest binding, we prepared a series of 12 deconstructed Hamilton receptors with varying degrees of steric bulk and preorganization. Both diethylbarbital and 3-methyl-7-propylxanthine were investigated as guests for the synthetic receptors. The stoichiometry of guest binding was investigated using Job plots for each host-guest pair, and H-1 NMR titrations were performed to measure the guest binding affinities. To complement the solution-state studies, DFT calculations at the B3LYP/6-31+G(d,p) level of theory employing the IEF-PCM CHCl3 solvation model were also performed. Calculated guest binding energies correlated well with the experimental findings and provided additional insight into the factors influencing guest binding. Taken together, the results presented highlight the interplay between preorganization and steric interactions in establishing favorable interactions for self-assembled hydrogen-bonded systems.

  DOI：

  10.1021/jo402500a

文献信息

• Understanding the Effects of Preorganization, Rigidity, and Steric Interactions in Synthetic Barbiturate Receptors
  作者：Jacqueline M. McGrath、Michael D. Pluth

  DOI：10.1021/jo402500a

  日期：2014.1.17

  Synthetic barbiturate receptors have been utilized for many applications due to their high binding affinities for complementary guests. Although interest in this class of receptors spans from supramolecular to materials chemistry, the effects of receptor steric bulk and preorganization on guest binding affinity has not been studied systematically. To investigate the roles that steric bulk and preorganization play in guest binding, we prepared a series of 12 deconstructed Hamilton receptors with varying degrees of steric bulk and preorganization. Both diethylbarbital and 3-methyl-7-propylxanthine were investigated as guests for the synthetic receptors. The stoichiometry of guest binding was investigated using Job plots for each host-guest pair, and H-1 NMR titrations were performed to measure the guest binding affinities. To complement the solution-state studies, DFT calculations at the B3LYP/6-31+G(d,p) level of theory employing the IEF-PCM CHCl3 solvation model were also performed. Calculated guest binding energies correlated well with the experimental findings and provided additional insight into the factors influencing guest binding. Taken together, the results presented highlight the interplay between preorganization and steric interactions in establishing favorable interactions for self-assembled hydrogen-bonded systems.