anthranilic acid-(4-nitro-benzylidenehydrazide) | 107410-44-6

• 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: anthranilic acid-(4-nitro-benzylidenehydrazide)
• 英文别名: Anthranilsaeure-(4-nitro-benzylidenhydrazid)；2-amino-N-[(E)-(4-nitrophenyl)methylideneamino]benzamide
• CAS: 107410-44-6
• 化学式: C₁₄H₁₂N₄O₃
• 分子量: 284.274
• InChiKey: AQGHEAFLSZVGEJ-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4-硝基苄基亚基)苯胺 、 2-氨基亚苯基肼 以 甲醇 为溶剂， 反应 2.0h， 生成 anthranilic acid-(4-nitro-benzylidenehydrazide)
  参考文献：
  名称：

  Fueloep, Ferenc; Simeonov, Mario; Pihlaja, Kalevi, Tetrahedron, 1992, vol. 48, # 3, p. 531 - 538

  摘要：

  DOI：

文献信息

• Correlation analysis of the13C chemical shifts of substituted benzaldehyde 2-aminobenzoylhydrazones. Study of the propagation of substituent effects along a heteroatomic chain
  作者：Kari Neuvonen、Ferenc F�l�p、Helmi Neuvonen、Mario Simeonov、Kalevi Pihlaja

  DOI：10.1002/(sici)1099-1395(199701)10:1<55::aid-poc854>3.0.co;2-d

  日期：1997.1

  The C-13 chemical shifts of eight series of para- or meta-substituted benzaldehyde 2-aminobenzoylhydrazones possessing both amide and imine functionalities were measured. The C-13 chemical shifts were used to study the transmission of electronic substituent effects along the heteroaromatic side-chain of the substituted aromatic ring, In addition to the C=N bond, the benzoylhydrazones possess in their side-chain polarizable C=O and phenyl pi-units. The benzylidenic ring-substituent chemical shifts were analysed by the dual substituent parameter approach to separate the inductive and resonance effects, The negative p(I) and p(R) values observed (i.e. reverse substituent effects) indicate a significant pi-polarization of the C=N bond, The highly negative p(R) values, especially those in the case of meta substitution, suggest a contribution from a marked secondary field-transmitted resonance effect, The results are compared with those obtained for other hydrazones or imines. Variation of the electron-withdrawing ability of the N-2 substituent is seen to have a systematic effect on the p(I) values. Reverse substituent effects are also observed at the C-1'' site of the 2-aminobenzoyl ring while C-4'' shifts show normal behaviour, consistent with the general concept of the pi-polarization that each pi-unit of the side-chain is polarized largely as a localized system, Accordingly, the pi-polarization effect is seen efficiently to propagate also along a heteroaromatic chain, On the other hand, the C=O sites exhibit normal, although fairly slight, dependence on the benzylidenic substituent indicating an insignificant role of pi-polarization at that site. The effects of the solvent, CDCI3 vs. DMSO-d(6), on the p(I) and p(R) values are also considered.
• Fueloep, Ferenc; Simeonov, Mario; Pihlaja, Kalevi, Tetrahedron, 1992, vol. 48, # 3, p. 531 - 538
  作者：Fueloep, Ferenc、Simeonov, Mario、Pihlaja, Kalevi

  DOI：——

  日期：——