2,4,6-trinitrophenyl 4-nitrobenzoate | 128015-99-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2,4,6-trinitrophenyl 4-nitrobenzoate
• 英文别名: picryl 4-nitrobenzoate；4-nitro-benzoic acid picryl ester；4-Nitro-benzoesaeure-picrylester；(2,4,6-Trinitrophenyl) 4-nitrobenzoate
• CAS: 128015-99-6
• 化学式: C₁₃H₆N₄O₁₀
• 分子量: 378.211
• InChiKey: AOPRVOIVQZMGPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 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：
  210
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,4,6-trinitrophenyl 4-nitrobenzoate 、 苯胺 以 甲醇 为溶剂， 生成 4-硝基苯甲酰替苯胺 、 2,4,6-三硝基二苯基胺 、 、 aniline picrate
  参考文献：
  名称：

  苯甲酸苄基酯在甲醇中的苯胺分解：反应性，区域选择性，动力学和机理

  摘要：

  甲醇中苯甲酸吡啶酯衍生物1a–g与苯胺在甲醇中的反应通过COO和ArO键的裂解途径进行。此外，这些酯对苯胺分解的反应性与每个酯的最高占据分子轨道苯胺和最低未占据分子轨道之间的能隙相关。还讨论了酰基氧对芳基氧裂解的区域选择性。整体速率常数ķ TOT分成ķ CO  Ô（酰基-氧裂解速率常数）和ķ氩 Ò（芳基氧裂解速率常数）。该CO 通过逐步机制O键裂解的进步，其中所述四面体中间体的形成是限速步骤。上述Ar  O键裂解继续通过A S Ñ其中所述离去基团从所述迈森海梅复杂离开其在速率决定步骤形成后迅速发生的Ar机制。

  DOI：

  10.1002/kin.20779
• 作为产物：
  描述：

  苦味酸 、 4-硝基苯甲酰氯 以 二氯甲烷 为溶剂， 生成 2,4,6-trinitrophenyl 4-nitrobenzoate
  参考文献：
  名称：

  Dell'Erba, Carlo; Sancassan, Fernando; Leandri, Giuseppe, Gazzetta Chimica Italiana, 1989, vol. 119, # 12, p. 643 - 648

  摘要：

  DOI：

文献信息

• Vogel,A.I., Text-Book of Practical Organic Chemistry, 1. Aufl. <London 1948> S. 653, 656, 3. Aufl. <London 1956> S. 682, 685
  作者：Vogel,A.I.

  DOI：——

  日期：——
• DFT calculations of 2,4,6-trinitrophenylbenzoate derivatives: Structure, ground state properties and spectral properties
  作者：Mahmoud F. Ibrahim、S.A. Senior、Mohamed A. El-atawy、Samir K. El-Sadany、Ezzat A. Hamed

  DOI：10.1016/j.molstruc.2011.09.024

  日期：2011.12

  2,4,6-Trinitrophenylbenzoate derivatives 3(a-g) were synthesised and their optimum molecular geometries, ground state properties, IR, UV and NMR spectra were calculated using the B3LYP method with 6-31G** Pople basis set. The predicted geometry showed that the aryl-oxygen bond is stronger than acyl-oxygen bond. Bond lengths are affected by the presence of electron donating or electron withdrawing groups in benzoyl moiety. The orientation of the two aryl rings with respect to each other is neither in the same plane nor perpendicular. Hammett plot showed good linearity between substituent constant and the HOMO as well as LUMO energies. Mulliken and NBO charges indicate that the carbonyl carbon (C7) is more positively charged than the ipso carbon (C10), while the inspection of the coefficient on the carbonyl carbon and the ipso carbon atom for LUMO showed that its value is greater for C10 compared to C7. The correlation between the experimental and the theoretical results indicates that density functional theory B3LYP method is able to provide satisfactory results for predicting IR., UV and NMR properties. Crown Copyright (C). 2011 Published by Elsevier B.V. All rights reserved.