| 1438243-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• CAS: 1438243-18-5
• 化学式: C₃₃H₂₃N₃O₄*H
• 分子量: 526.571
• InChiKey: WVSKUXDFODSCKE-ZAIIWXDFSA-O

反应信息

• 作为产物：
  描述：

  N-(2-phenyloxylphenyl)maleimide 在 甲烷磺酸 作用下， 以 氘代二甲亚砜 、 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Comprehensive Experimental Study of N-Heterocyclic π-Stacking Interactions of Neutral and Cationic Pyridines

  摘要：

  A comprehensive experimental study was carried out by measuring the relative strengths of parallel pi-stacking interactions of N-heterocycles with nonheterocycles. A versatile and rigid model system was developed, which was in equilibrium between a "closed" conformation that forms an intramolecular pi-stacking interaction and an "open" conformation that cannot form the interaction. First, the formation and geometries of the intramolecular N-heterocyclic pi-stacking interactions were verified by X-ray crystallography. Next, the closed/open ratios were measured in solution via integration of the H-1 NMR spectra, providing an accurate comparison of the N-heterocyclic pi-stacking interactions. The synthetic versatility of this model system enabled the systematic and comprehensive comparison of the influences of position, charge, and substituent effects of the nitrogen atom of the N-heterocycles within a single model system. The pi-stacking interactions of the neutral N-heterocyclic rings were slightly stronger than that of nonheterocyclic rings. Cationic N-heterocycles formed significantly stronger pi-stacking interactions than neutral N-heterocycles. The position of the nitrogen atom also had a strong influence on the stability of N-heterocyclic pi-stacking complexes. Interestingly, opposite stability trends were observed for neutral and cationic N-heterocycles. For neural N-heterocycles, geometries with the nitrogen away from the pi-face of the opposing ring were the more stable. For cationic N-heterocycles, geometries with the nitrogen close to the pi-face of the opposing ring were the more stable. Finally, N-methylated heterocycles consistently formed stronger pi-stacking interactions than N-protonated heterocycles.

  DOI：

  10.1021/jo400370e