[(15)N]-1-nitro-3,5-bis(trifluoromethyl)benzene | 1046423-92-0

• 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: [(15)N]-1-nitro-3,5-bis(trifluoromethyl)benzene
• CAS: 1046423-92-0
• 化学式: C₈H₃F₆NO₂
• 分子量: 260.101
• InChiKey: GMUWJDVVXLBMEZ-XPOOIHDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [(15)N]-1-nitro-3,5-bis(trifluoromethyl)benzene 在 盐酸 、 tin(II) chloride dihydrate 作用下， 生成 [(15)N]-3,5-bis(trifluoromethyl)anilinne
  参考文献：
  名称：

  Edge‐to‐Face CH/π Aromatic Interaction and Molecular Self‐Recognition inepi‐Cinchona‐Based Bifunctional Thiourea Organocatalysis

  摘要：

  AbstractThe impact of cooperativity between intermolecular interactions is demonstrated by the molecular self‐recognition properties of highly enantioselective epi‐cinchona bifunctional thiourea organocatalysts. Low‐temperature NMR experiments in inert solvents have revealed two sets of nonequivalent resonances in equal population for thiourea‐modified members of the epi‐quinine and epi‐quinidine families. In solution, the predominance of an asymmetric (C1) dimeric self‐assembly with noteworthy structural motifs became evident: simultaneous intra‐ and intermolecular thiourea hydrogen bonding and a CH/π interaction were observed. Both the stereochemical and the diverse conformational features of the system favor the observed quinoline T‐shaped aromatic π–π stacking interaction. The structure findings are supported by quantitative proton–proton distance data that were available from NOE buildup curves. The 3D structure of the dimeric assembly has been modeled in agreement with the H–H distance restraints. Owing to the geometrical preference associated with the dimerization process, the self‐assembled bifunctional system is interpreted as a charge‐transfer complex with the potential for catalyst self‐activation.

  DOI：

  10.1002/chem.200800197
• 作为产物：
  描述：

  间二三氟甲苯 在 硝酸钾-15N 、 oleum 作用下， 以 硫酸 为溶剂， 生成 [(15)N]-1-nitro-3,5-bis(trifluoromethyl)benzene
  参考文献：
  名称：

  Edge‐to‐Face CH/π Aromatic Interaction and Molecular Self‐Recognition inepi‐Cinchona‐Based Bifunctional Thiourea Organocatalysis

  摘要：

  AbstractThe impact of cooperativity between intermolecular interactions is demonstrated by the molecular self‐recognition properties of highly enantioselective epi‐cinchona bifunctional thiourea organocatalysts. Low‐temperature NMR experiments in inert solvents have revealed two sets of nonequivalent resonances in equal population for thiourea‐modified members of the epi‐quinine and epi‐quinidine families. In solution, the predominance of an asymmetric (C1) dimeric self‐assembly with noteworthy structural motifs became evident: simultaneous intra‐ and intermolecular thiourea hydrogen bonding and a CH/π interaction were observed. Both the stereochemical and the diverse conformational features of the system favor the observed quinoline T‐shaped aromatic π–π stacking interaction. The structure findings are supported by quantitative proton–proton distance data that were available from NOE buildup curves. The 3D structure of the dimeric assembly has been modeled in agreement with the H–H distance restraints. Owing to the geometrical preference associated with the dimerization process, the self‐assembled bifunctional system is interpreted as a charge‐transfer complex with the potential for catalyst self‐activation.

  DOI：

  10.1002/chem.200800197