2,6-Naphthalenediol, 1,5-bis[(benzylimino)methyl]-

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-Naphthalenediol, 1,5-bis[(benzylimino)methyl]-
• 英文别名: 1,5-bis(benzyliminomethyl)naphthalene-2,6-diol
• 化学式: C₂₆H₂₂N₂O₂
• 分子量: 394.473
• InChiKey: HBUOCTZMDJHLOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  2,6-二醛基-1,5-二羟基萘 、 苄胺 以 氘代甲醇-d 为溶剂， 以96%的产率得到2,6-Naphthalenediol, 1,5-bis[(benzylimino)methyl]-
  参考文献：
  名称：

  Mutual Interference between Intramolecular Proton Transfer Sites through the Adjoining π-Conjugated System in Schiff Bases of Double-Headed, Fused Salicylaldehydes

  摘要：

  We synthesized two constitutionally isomeric bis(iminomethyl)-2,6-dihydroxynaphthalenes, namely, alpha,alpha-diimines 1 and beta,beta-diimines 2, which can be formally represented as fused salicylaldimines with resonance-assisted hydrogen-bonding sites. Spectroscopic data show that the OH/OH, NH/OH, and NH/NH forms of 1 were in equilibrium in solution and that the proportion of the NH-bearing tautomers increased as the solvent polarity increased. The UV spectra of thin solid films of 1 with various types of hydrogen-bonding networks differed from one another, and the spectral profiles were markedly temperature dependent, whereas the spectra of 1 in the molten state showed quite similar profiles. In contrast, 2 existed predominantly as the OH/OH form irrespective of the solvent polarity or crystal packing. Quantum chemical calculations suggest that the difference between the probabilities of intramolecular proton transfer in 1 and 2 can be explained in terms of the interplay between the resonance-assisted hydrogen-bonding sites and the adjoining pi-conjugated system.

  DOI：

  10.1021/jo401108z