N,N'-bis(4-hydroxybenzaldehyde)-1,3-propandiimine | 126948-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N'-bis(4-hydroxybenzaldehyde)-1,3-propandiimine
• 英文别名: N,N'-bis(p-hydroxybenzylidene)-1,3-diaminopropane；Phenol, 4,4'-(1,3-propanediylbis(nitrilomethylidyne))bis-；4-[3-[(4-hydroxyphenyl)methylideneamino]propyliminomethyl]phenol
• CAS: 126948-53-6
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: NONXHPQRMNHCIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯甲醛 、 1,3-丙二胺 以 甲醇 为溶剂， 反应 2.0h， 生成 N,N'-bis(4-hydroxybenzaldehyde)-1,3-propandiimine
  参考文献：
  名称：

  1,3-二氨基丙烷与芳族醛的反应中环化与双亚胺形成之间的竞争

  摘要：

  1,3-二胺与醛或酮的缩合产生两种主要产物，即六氢嘧啶和双亚胺。一系列芳族醛与1,3-二氨基丙烷或1,3-二氨基-2-丙醇之间反应的实验研究表明，六氢嘧啶受亲核性较弱的胺和芳环上存在吸电子基团的影响醛。计算表明该芳基环取代基的电子性质既影响最终产物的相对热力学稳定性，也影响醛作为亲电子试剂的反应性。

  DOI：

  10.1016/j.tet.2009.10.060

文献信息

• Effect of hydroxyl group position on adsorption behavior and corrosion inhibition of hydroxybenzaldehyde Schiff bases: Electrochemical and quantum calculations
  作者：I. Danaee、O. Ghasemi、G.R. Rashed、M. Rashvand Avei、M.H. Maddahy

  DOI：10.1016/j.molstruc.2012.11.013

  日期：2013.3

  The corrosion inhibition and adsorption of N,N'-bis(n-hydroxybenzaldehyde)-1,3-propandiimine (n-HBP) Schiff bases has been investigated on steel electrode in 1 M HCl by using electrochemical techniques. The experimental results suggest that the highest inhibition efficiency was obtained for 3-HBP. Polarization curves reveal that all studied inhibitors are mixed type. Density functional theory (DFT) at the B3LYP/6-31G(d,p) and B3LYP/3-21G basis set levels and ab initio calculations using HF/6-31G(d,p) and HF/3-21G methods were performed on three Schiff bases. By studying the effects of hydroxyl groups in ortho-, meta-, para- positions, the best one as inhibitor was found to be meta-position of OH in Schiff base (i.e., 3-HBP). The order of inhibition efficiency obtained was corresponded with the order of most of the calculated quantum chemical parameters. Quantitative structure activity relationship (QSAR) approach has been used and a correlation of the composite index of some of the quantum chemical parameters was performed to characterize the inhibition performance of the Schiff bases studied. The results showed that %IE of the Schiff bases was closely related to some of the quantum chemical parameters but with varying degrees/order. The calculated %IE of the Schiff base studied was found to be close to their experimental corrosion inhibition efficiencies. (c) 2012 Elsevier B.V. All rights reserved.
• Competition between cyclisation and bisimine formation in the reaction of 1,3-diaminopropanes with aromatic aldehydes
  作者：Julie M. Locke、Renate Griffith、Trevor D. Bailey、Robyn L. Crumbie

  DOI：10.1016/j.tet.2009.10.060

  日期：2009.12

  Condensation of 1,3-diamines with aldehydes or ketones gives rise to two major products, the hexahydropyrimidine and the bisimine. Experimental studies of the reaction between a range of aromatic aldehydes and 1,3-diaminopropane or 1,3-diamino-2-propanol establish that the hexahydropyrimidine is favoured by the less nucleophilic amine and by the presence of electron withdrawing groups on the aryl ring

  1,3-二胺与醛或酮的缩合产生两种主要产物，即六氢嘧啶和双亚胺。一系列芳族醛与1,3-二氨基丙烷或1,3-二氨基-2-丙醇之间反应的实验研究表明，六氢嘧啶受亲核性较弱的胺和芳环上存在吸电子基团的影响醛。计算表明该芳基环取代基的电子性质既影响最终产物的相对热力学稳定性，也影响醛作为亲电子试剂的反应性。