2-(chloromercurio)-4-iodo-N-(4-nitrobenzylidene)aniline | 144271-75-0

• 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: 2-(chloromercurio)-4-iodo-N-(4-nitrobenzylidene)aniline
• 英文别名: chloro-[5-iodo-2-[(4-nitrophenyl)methylideneamino]phenyl]mercury
• CAS: 144271-75-0
• 化学式: C₁₃H₈ClHgIN₂O₂
• 分子量: 587.166
• InChiKey: IUHBYFJDMHVITK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  4-iodo-N-(4-nitrobenzylidene)aniline 、 mercury(II) diacetate 在 lithium chloride 作用下， 以 甲醇 为溶剂， 以78%的产率得到2-(chloromercurio)-4-iodo-N-(4-nitrobenzylidene)aniline
  参考文献：
  名称：

  Mercuration of Schiff bases of substituted benzylideneanilines

  摘要：

  As part of an effort to investigate substituent effects on the intramolecular coordination between N and Hg, the mercuration of 36 substituted benzylideneanilines was studied. The structure characterization of the products by IR, H-1 NMR, C-13 NMR, and MS indicates that for all of the reactions examined, the mercury is directed to the ortho position of the N-phenyl ring or the para position of the N-phenyl ring when these sites are not occupied by a substituent. The position of the HgCl group in the mercurated product of N-(4-nitrobenzylidene)-beta-naphthylamine has been confirmed by single-crystal X-ray determination, which also provided circumstantial evidence for the existence of the N--> Hg intramolecular coordination with a four-membered ring. The possible mechanism of the reaction was proposed, in which the mercuration at the ortho position of the N-phenyl ring was facilitated by the imino moiety upon formation of a coordination complex with Hg(OAc)2 in the first step, followed by a subsequent electrophilic substitution at the ortho position of the N-phenyl ring. This reaction is different from the metalation of benzylideneanilines by transition metals, in which the metal atom is usually directed to the ortho position of the C-phenyl ring, and provides a new example of the so-called 'cyclometalation" reaction.

  DOI：

  10.1021/om00059a058