2,4-dinitrophenyl methanesulfonate | 7155-37-5

• 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: 2,4-dinitrophenyl methanesulfonate
• 英文别名: methanesulfonic acid-(2,4-dinitro-phenyl ester)；Methansulfonsaeure-(2,4-dinitro-phenylester)；(2,4-Dinitrophenyl) methanesulfonate
• CAS: 7155-37-5
• 化学式: C₇H₆N₂O₇S
• 分子量: 262.2
• InChiKey: OBNLOECNGJKOMP-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  456.2±45.0 °C(Predicted)
• 密度：
  1.657±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4-dinitrophenyl methanesulfonate 在 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2,4-二硝基苯酚(1-)
  参考文献：
  名称：

  Pitfalls in Assessing the α-Effect: Reactions of Substituted Phenyl Methanesulfonates with HOO⁻, OH⁻, and Substituted Phenoxides in H₂O

  摘要：

  Toward resolving the current controversy regarding the validity of the a-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-11 with HOO-, OH,- and Z-substituted phenoxides in the gas phase versus solution (H2O). Criteria examined in this work are the following: (1) Bronsted-type and Hammett plots for reactions with HOO- and OH-, (2) comparison of beta(lg) values reported previously for the reactions of Y-substituted phenyl benzenesulfonates 2a-2k with HOO- (beta(lg) = -0.73) and OH- (beta(lg) = -0.55), and for those of 1a-11 with HOO- (beta(lg) = -0.69) and OH- (beta(lg) = -1.35), and (3) Bronsted-type plot showing extreme deviation of OH- for reactions of 2,4-dintrophenyl methanesulfonate la with aryloxides, HOO-, and OH-, signifying extreme solvation vs different mechanisms. The results reveal significant pitfalls in assessing the validity of current interpretations of the alpha-effect. The extreme negative deviation by OH- must be due, in part, to the difference in their reaction mechanisms. Thus, the apparent dependence of the alpha-effect on leaving-group basicity found in this study has no significant meaning due to the difference in operating mechanisms. The current results argue in favor of a further criterion, i.e., a consistency in mechanism for the alpha-nucleophiles and normal nucleophiles.

  DOI：

  10.1021/jo101978x
• 作为产物：
  描述：

  甲磺酸苯酯 在 硫酸 、 potassium nitrate 作用下， 生成 2,4-dinitrophenyl methanesulfonate
  参考文献：
  名称：

  Schall, Journal fur praktische Chemie (Leipzig 1954), 1893, vol. <2> 48, p. 243

  摘要：

  DOI：

文献信息

• THE ESTERIFICATION OF CERTAIN NITROPHENOLS WITH METHANESULFONYL CHLORIDE
  作者：JAMES H. LOOKER

  DOI：10.1021/jo01137a029

  日期：1952.3
• Vizgert,R.V. et al., Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 1259 - 1263
  作者：Vizgert,R.V. et al.

  DOI：——

  日期：——
• KURTS A. L.; KOGAN G. O.; BUNDEL YU. G., BECTH. MGU. XIMIYA, 1981, 22, HO 1, 86-91
  作者：KURTS A. L.、 KOGAN G. O.、 BUNDEL YU. G.

  DOI：——

  日期：——
• Pitfalls in Assessing the α-Effect: Reactions of Substituted Phenyl Methanesulfonates with HOO⁻, OH⁻, and Substituted Phenoxides in H₂O
  作者：Ik-Hwan Um、Li-Ra Im、Erwin Buncel

  DOI：10.1021/jo101978x

  日期：2010.12.17

  Toward resolving the current controversy regarding the validity of the a-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-11 with HOO-, OH,- and Z-substituted phenoxides in the gas phase versus solution (H2O). Criteria examined in this work are the following: (1) Bronsted-type and Hammett plots for reactions with HOO- and OH-, (2) comparison of beta(lg) values reported previously for the reactions of Y-substituted phenyl benzenesulfonates 2a-2k with HOO- (beta(lg) = -0.73) and OH- (beta(lg) = -0.55), and for those of 1a-11 with HOO- (beta(lg) = -0.69) and OH- (beta(lg) = -1.35), and (3) Bronsted-type plot showing extreme deviation of OH- for reactions of 2,4-dintrophenyl methanesulfonate la with aryloxides, HOO-, and OH-, signifying extreme solvation vs different mechanisms. The results reveal significant pitfalls in assessing the validity of current interpretations of the alpha-effect. The extreme negative deviation by OH- must be due, in part, to the difference in their reaction mechanisms. Thus, the apparent dependence of the alpha-effect on leaving-group basicity found in this study has no significant meaning due to the difference in operating mechanisms. The current results argue in favor of a further criterion, i.e., a consistency in mechanism for the alpha-nucleophiles and normal nucleophiles.
• Schall, Journal fur praktische Chemie (Leipzig 1954), 1893, vol. <2> 48, p. 243
  作者：Schall

  DOI：——

  日期：——