4-bromo-2-[(propylamino)methyl]phenol | 1240568-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-2-[(propylamino)methyl]phenol
• 英文别名: 4-Bromo-2-[(aminopropyl)methyl]-phenol；4-bromo-2-[(propylazaniumyl)methyl]phenolate
• CAS: 1240568-03-9
• 化学式: C₁₀H₁₄BrNO
• 分子量: 244.131
• InChiKey: BHOOUCPLMCUSLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-propyl-5-bromosalicylideneimine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以1.48 g的产率得到4-bromo-2-[(propylamino)methyl]phenol
  参考文献：
  名称：

  Intermolecular Interactions in the Solid State of Ionic Secondary Mannich Bases

  摘要：

  Two new secondary Mannich bases, 4-bromo-2-[(aminopropyl)methyl]-phenol (1) and 4-nitro-2-[(aminopropyl)methyll-phenol (2), were synthesized. Crystal structures were determined at liquid nitrogen temperature. It was found that in both compounds the proton transfer forms exist in the solid state. In the case of 1, this was unexpected, because of the weak acidity of p-bromophenol being the parent component of this Mannich base. The reason for that was found to be the formation of the O-center dot center dot center dot H-N+ hydrogen bonded tetramer in the solid state. Two cyclic aggregates R-4(2)(8) and R-2(2)(12) describe the pattern of hydrogen bonded interactions in the crystals of both compounds. Additionally, C-H center dot center dot center dot pi interactions stabilize the crystal structures. The hydrogen bonds in I are slightly stronger (N center dot center dot center dot O distances 2.708 and 2.733 angstrom) than in 2 (2.721 and 2.765 angstrom, respectively) despite the fact that p-nitrophenol participating in 2 is a stronger acid. The influence of permittivity of surroundings and the hydrogen bonding pattern on the properties of intermolecular hydrogen bonds are discussed on the basis of B3LYP and MP2 calculations with basis sets 6-31+G(d,p) and 6-31++G(2d,2p). The coupling between hydrogen bonds in crystals was studied with the application of the IR spectra of isotopically diluted species. It was found that such a coupling is stronger for 2, forming weaker hydrogen bonds. Both the theory of IR spectra and quantum chemical calculations demonstrate that the source of the observed behavior is electronic participation in vibronic absorption.

  DOI：

  10.1021/cg201179x