1,3-二乙酰氧基-4,6-二硝基苯 | 678148-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 1,3-二乙酰氧基-4,6-二硝基苯
• 英文名称: 1,3-diacetoxy-4,6-dinitrobenzene
• 英文别名: 1,5-diacetoxy-2,4-dinitro-benzene；1,5-Diacetoxy-2,4-dinitro-benzol；4.6-Dinitro-resorcindiacetat；(5-Acetyloxy-2,4-dinitrophenyl) acetate；(5-acetyloxy-2,4-dinitrophenyl) acetate
• CAS: 678148-37-3
• 化学式: C₁₀H₈N₂O₈
• 分子量: 284.182
• InChiKey: CZMAWJQHBYVWDN-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C(Solv: ethanol (64-17-5))
• 沸点：
  438.9±45.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-二乙酰氧基-4,6-二硝基苯 在 盐酸 作用下， 以 水 为溶剂， 以14%的产率得到4,6-二硝基间苯二酚
  参考文献：
  名称：

  Intramolecular hydrogen bonding and molecular geometry of 4,6-dinitroresorcinol from gas-phase electron diffraction

  摘要：

  The molecular geometry of 4,6-dinitroresorcinol has been determined by gas-phase electron diffraction. The resonance-assisted intramolecular hydrogen bonding is accompanied by pronounced bond length changes as compared with the parent molecules phenol and nitrobenzene. The molecular geometry is characterized by the following bond lengths (r(g)) and bond angles: (C-H)(mean), 1.086 +/- 0.015 Angstrom; (C-C)(mean), 1.402 +/- 0.003 Angstrom; C-3-C-4, 1.424 +/- 0.005 Angstrom; C-O, 1.341 +/- 0.004 Angstrom; O-H, 1.002 +/- 0.009 Angstrom; C-N, 1.461 +/- 0.004 Angstrom; (N-O)(mean), 1.233 +/- 0.003 Angstrom; angle C-1-C-2-C-3, 120.3 +/- 0.4 degrees; angle C-2-C-3-C-4, 119.3 +/- 0.3 degrees; angle C-3-C-4-C-5, 121.6 +/- 0.3 degrees; angle C-4-C-5-C-6, 118.0 +/- 0.4 degrees; angle C-4-C-3-O, 123.4 +/- 0.3 degrees; angle C-O-H, 104.5 +/- 1.4 degrees; angle C-3-C-4-N, 121.0 +/- 0.2 degrees; (angle C-N-O)(mean), 118.1 +/- 0.1 degrees; angle O-N-O, 123.7 +/- 0.2 degrees. The effective angle of nitro group torsion from electron diffraction is 14.4 +/- 1.3 degrees. If it is assumed that this effective angle of torsion emerges as a consequence of torsional vibrations about the planar equilibrium conformation, then a barrier to internal rotation of 18 +/- 3 kJ/mol may be estimated, the same as in nitrobenzene, the planarity of which is consistent with microwave spectroscopic results.

  DOI：

  10.1021/j100038a010
• 作为产物：
  描述：

  1,3-二乙酰氧基苯 在 硝酸 作用下， 反应 1.33h， 生成 1,3-二乙酰氧基-4,6-二硝基苯
  参考文献：
  名称：

  Intramolecular hydrogen bonding and molecular geometry of 4,6-dinitroresorcinol from gas-phase electron diffraction

  摘要：

  The molecular geometry of 4,6-dinitroresorcinol has been determined by gas-phase electron diffraction. The resonance-assisted intramolecular hydrogen bonding is accompanied by pronounced bond length changes as compared with the parent molecules phenol and nitrobenzene. The molecular geometry is characterized by the following bond lengths (r(g)) and bond angles: (C-H)(mean), 1.086 +/- 0.015 Angstrom; (C-C)(mean), 1.402 +/- 0.003 Angstrom; C-3-C-4, 1.424 +/- 0.005 Angstrom; C-O, 1.341 +/- 0.004 Angstrom; O-H, 1.002 +/- 0.009 Angstrom; C-N, 1.461 +/- 0.004 Angstrom; (N-O)(mean), 1.233 +/- 0.003 Angstrom; angle C-1-C-2-C-3, 120.3 +/- 0.4 degrees; angle C-2-C-3-C-4, 119.3 +/- 0.3 degrees; angle C-3-C-4-C-5, 121.6 +/- 0.3 degrees; angle C-4-C-5-C-6, 118.0 +/- 0.4 degrees; angle C-4-C-3-O, 123.4 +/- 0.3 degrees; angle C-O-H, 104.5 +/- 1.4 degrees; angle C-3-C-4-N, 121.0 +/- 0.2 degrees; (angle C-N-O)(mean), 118.1 +/- 0.1 degrees; angle O-N-O, 123.7 +/- 0.2 degrees. The effective angle of nitro group torsion from electron diffraction is 14.4 +/- 1.3 degrees. If it is assumed that this effective angle of torsion emerges as a consequence of torsional vibrations about the planar equilibrium conformation, then a barrier to internal rotation of 18 +/- 3 kJ/mol may be estimated, the same as in nitrobenzene, the planarity of which is consistent with microwave spectroscopic results.

  DOI：

  10.1021/j100038a010

文献信息

• Heller; Sourlis, Chemische Berichte, 1910, vol. 43, p. 2583
  作者：Heller、Sourlis

  DOI：——

  日期：——
• Intramolecular hydrogen bonding and molecular geometry of 4,6-dinitroresorcinol from gas-phase electron diffraction
  作者：Konstantin B. Borisenko、Karoly Zauer、Istvan Hargittai

  DOI：10.1021/j100038a010

  日期：1995.9

  The molecular geometry of 4,6-dinitroresorcinol has been determined by gas-phase electron diffraction. The resonance-assisted intramolecular hydrogen bonding is accompanied by pronounced bond length changes as compared with the parent molecules phenol and nitrobenzene. The molecular geometry is characterized by the following bond lengths (r(g)) and bond angles: (C-H)(mean), 1.086 +/- 0.015 Angstrom; (C-C)(mean), 1.402 +/- 0.003 Angstrom; C-3-C-4, 1.424 +/- 0.005 Angstrom; C-O, 1.341 +/- 0.004 Angstrom; O-H, 1.002 +/- 0.009 Angstrom; C-N, 1.461 +/- 0.004 Angstrom; (N-O)(mean), 1.233 +/- 0.003 Angstrom; angle C-1-C-2-C-3, 120.3 +/- 0.4 degrees; angle C-2-C-3-C-4, 119.3 +/- 0.3 degrees; angle C-3-C-4-C-5, 121.6 +/- 0.3 degrees; angle C-4-C-5-C-6, 118.0 +/- 0.4 degrees; angle C-4-C-3-O, 123.4 +/- 0.3 degrees; angle C-O-H, 104.5 +/- 1.4 degrees; angle C-3-C-4-N, 121.0 +/- 0.2 degrees; (angle C-N-O)(mean), 118.1 +/- 0.1 degrees; angle O-N-O, 123.7 +/- 0.2 degrees. The effective angle of nitro group torsion from electron diffraction is 14.4 +/- 1.3 degrees. If it is assumed that this effective angle of torsion emerges as a consequence of torsional vibrations about the planar equilibrium conformation, then a barrier to internal rotation of 18 +/- 3 kJ/mol may be estimated, the same as in nitrobenzene, the planarity of which is consistent with microwave spectroscopic results.