2-(chloromercurio)-N-(benzylidene)-4-toluidine | 144271-78-3

• 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)-N-(benzylidene)-4-toluidine
• 英文别名: [2-(benzylideneamino)-5-methylphenyl]-chloromercury
• CAS: 144271-78-3
• 化学式: C₁₄H₁₂ClHgN
• 分子量: 430.299
• InChiKey: DYGZILCMXTUSFY-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

• 作为反应物：
  描述：

  tin 、 2-(chloromercurio)-N-(benzylidene)-4-toluidine 以 xylene 为溶剂， 以64%的产率得到dichlorobis{2-(benzylideneamino)-5-tolyl}tin(IV)
  参考文献：
  名称：

  Transmetallation reaction of Schiff-base-type arylmercury compounds with metallic tin

  摘要：

  DOI：

  10.1016/0022-328x(93)83401-g
• 作为产物：
  描述：

  mercury(II) diacetate 、 N亚苄基对甲苯胺 在 lithium chloride 作用下， 以 甲醇 为溶剂， 以70%的产率得到2-(chloromercurio)-N-(benzylidene)-4-toluidine
  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

文献信息

• Transmetallation reaction of Schiff-base-type arylmercury compounds with 4-ethoxyphenyltellurium(IV) trichloride and the crystal structure of (4-ethoxyphenyl)[(2-benzylideneamino-5-methyl)phenyl]tellurium(IV) dichloride
  作者：Wu Yangjie、Ding Kuiling、Wang Yang、Zhu Ying、Yang Li

  DOI：10.1016/0022-328x(94)80024-3

  日期：1994.4

  diaryltellurium dichlorides prepared were characterized by elemental analysis, IR, 1H nuclear magnetic resonance and mass spectroscopy. The crystal structure of (4-ethoxyphenyl) [(2-benzylideneamino-5-methyl)phenyl]tellurium dichloride shows that the coordination on tellurium can be considered as essentially pseudo-octahedral, with lone pair electrons occupying the forth equatorial site. The TeN distance

  通过席夫碱型芳基汞化合物与4-乙氧基苯基碲三氯化物的金属转移反应，合成了一系列新的不对称二芳基二氯化碲。制备的所有不对称二芳基二氯化碲均通过元素分析（IR，1）进行表征H核磁共振和质谱。（4-乙氧基苯基）[（2-苄叉基氨基-5-甲基）苯基]二氯化碲的晶体结构表明，碲上的配位可被认为是基本上伪八面体，孤对电子占据了赤道第四个位点。TeN距离为2.905（2）Å，比Te和N的范德华半径之和（约3.7Å）短，表明Te和N之间存在大量次要分子内配位。N→Te分子内配位成立希夫碱部分呈近平面几何形状。