N,N'-di-[2]naphthyl-methylenediamine | 500535-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-di-[2]naphthyl-methylenediamine
• 英文别名: N,N'-Di-[2]naphthyl-methylendiamin；Bis-(β-naphthylamino)-methan；Methylen-di-β-naphthylamin；Methanediamine, N,N'-di-2-naphthalenyl-；N,N'-dinaphthalen-2-ylmethanediamine
• CAS: 500535-47-7
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: WVCPMBHZPSBORV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 2-萘胺 在 丙酮 作用下， 生成 N,N'-di-[2]naphthyl-methylenediamine
  参考文献：
  名称：

  Moehlau; Haase, Chemische Berichte, 1902, vol. 35, p. 4164

  摘要：

  DOI：

文献信息

• Experimental, Spectroscopic, and Computational Insights into the Reactivity of “Methanal” with 2-Naphthylamines
  作者：Martin Havlík、Tereza Navrátilová、Michaela Drozdová、Ameneh Tatar、Priscila A. Lanza、Diego Dusso、Elizabeth Laura Moyano、Carlos A. Chesta、Domingo Mariano A. Vera、Bohumil Dolenský

  DOI：10.3390/molecules28041549

  日期：——

  The reactions of 2-naphthylamine and methyl 6-amino-2-naphthoate with formalin and paraformaldehyde were studied experimentally, spectrally, and by quantum chemical calculations. It was found that neither the corresponding aminals nor imines were formed under the described conditions but could be prepared and spectrally characterized at least in situ under modified conditions. Several of the previously undescribed intermediates and by-products were isolated or at least spectrally characterized. First principle density functional theory (DFT) calculations were performed to shed light on the key aspects of the thermochemistry of decomposition and further condensation of the corresponding aminals and imines. The calculations also revealed that the electrophilicity of methanal was significantly greater than that of ordinary oxo-compounds, except for perfluorinated ones. In summary, methanal was not behaving as the simplest aldehyde but as a very electron-deficient oxo-compound.

  通过实验、光谱和量子化学计算研究了 2-萘胺和 6-氨基-2-萘甲酸甲酯与福尔马林和多聚甲醛的反应。结果发现，在所述条件下既不会形成相应的氨基，也不会形成亚胺，但至少可以在改良条件下就地制备并从光谱上确定其特征。一些以前未曾描述过的中间产物和副产物被分离出来，或至少在光谱上得到了表征。我们进行了第一原理密度泛函理论（DFT）计算，以揭示相应的氨基和亚胺分解和进一步缩合的热化学过程的关键方面。计算还表明，除全氟化合物外，甲缩醛的亲电性明显高于普通氧化化合物。总之，甲缩醛并不像最简单的醛，而是一种非常缺电子的氧化化合物。
• Morgan, Journal of the Chemical Society, 1898, vol. 73, p. 546,547, 549
  作者：Morgan

  DOI：——

  日期：——