N-2,6-difluorobenzylidene-2-phenylaniline

• 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: N-2,6-difluorobenzylidene-2-phenylaniline
• 英文别名: 1-(2,6-difluorophenyl)-N-(2-phenylphenyl)methanimine
• 化学式: C₁₉H₁₃F₂N
• 分子量: 293.316
• InChiKey: KVCOVSRVZDWNQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-2,6-difluorobenzylidene-2-phenylaniline 以 乙醇 、 溶剂黄146 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Steric and electronic effects on E/Z composition of exocyclic cyclopalladated N-benzylideneamines

  摘要：

  Exocyclic six-membered cyclopalladated dimers 2a-2c, [Pd(C-N)Br](2) have been prepared by reaction of palladium(II) acetate with N-benzylidene-2-phenylanilines 1a-1c, RCH = NC(6)H(4)-2-C(6)H(5) {1a, R = 2,6-Cl(2)C(6)H(3); 1b, R = 2,6-F(2)C(6)H(3) and 1c, R = 2,4,6-(CH(3)O)(3)C(6)H(2)}, and a subsequent metathesis reaction with LiBr. Reaction of 2 with PPh(3) produced mononuclear compounds 3, [Pd(C-N)Br(PPh(3))]. Analysis of the (1)H NMR methinic region of 2 and 3 revealed their E/Z composition. 2a and 2b present imines in E and Z configuration in an approximate ratio of 1:1, white 2c consists almost exclusively of imines in E configuration. Compounds 3 also present imines in E and Z configuration, the former are more abundant in all cases (greater than or equal to 4:1). The crystal structure of 3c with the imine in E configuration has been determined. It crystallizes in the monoclinic space group P2(1)/a with a = 19.258(3) Angstrom, b = 13.177(2) Angstrom, c = 14.660(2) Angstrom and beta = 113.78(2)degrees. Steric and electronic effects on the E/Z composition of 2 and 3 and related exocyclic cyclopalladated N-benzylidenebenzylamines suggest that, for compounds of this type, the E --> Z isomerization takes place via a rotation through the N = C bond which is assisted by pi back bonding of the palladium(II) center to the iminic function. (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(97)00232-5

文献信息

• Steric and electronic effects on E/Z composition of exocyclic cyclopalladated N-benzylideneamines
  作者：Joan Albert、Jaume Granell、Anna Luque、Mercè Font-Bardía、Xavier Solans

  DOI：10.1016/s0022-328x(97)00232-5

  日期：1997.1

  Exocyclic six-membered cyclopalladated dimers 2a-2c, [Pd(C-N)Br](2) have been prepared by reaction of palladium(II) acetate with N-benzylidene-2-phenylanilines 1a-1c, RCH = NC(6)H(4)-2-C(6)H(5) 1a, R = 2,6-Cl(2)C(6)H(3); 1b, R = 2,6-F(2)C(6)H(3) and 1c, R = 2,4,6-(CH(3)O)(3)C(6)H(2)}, and a subsequent metathesis reaction with LiBr. Reaction of 2 with PPh(3) produced mononuclear compounds 3, [Pd(C-N)Br(PPh(3))]. Analysis of the (1)H NMR methinic region of 2 and 3 revealed their E/Z composition. 2a and 2b present imines in E and Z configuration in an approximate ratio of 1:1, white 2c consists almost exclusively of imines in E configuration. Compounds 3 also present imines in E and Z configuration, the former are more abundant in all cases (greater than or equal to 4:1). The crystal structure of 3c with the imine in E configuration has been determined. It crystallizes in the monoclinic space group P2(1)/a with a = 19.258(3) Angstrom, b = 13.177(2) Angstrom, c = 14.660(2) Angstrom and beta = 113.78(2)degrees. Steric and electronic effects on the E/Z composition of 2 and 3 and related exocyclic cyclopalladated N-benzylidenebenzylamines suggest that, for compounds of this type, the E --> Z isomerization takes place via a rotation through the N = C bond which is assisted by pi back bonding of the palladium(II) center to the iminic function. (C) 1997 Elsevier Science S.A.