2-chloro-4-nitrophenyl methanesulfonate | 55027-13-9

• 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-chloro-4-nitrophenyl methanesulfonate
• 英文别名: 3-chloro-4-methylsulfonyloxy-nitrobenzene；(2-Chloro-4-nitrophenyl) methanesulfonate
• CAS: 55027-13-9
• 化学式: C₇H₆ClNO₅S
• 分子量: 251.647
• InChiKey: HMKBKTADOAMDEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 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：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-4-nitrophenyl methanesulfonate 在 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 2-氯-4-硝基苯酚
  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：

  2-氯-4-硝基苯酚 、 甲基磺酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2-chloro-4-nitrophenyl methanesulfonate
  参考文献：
  名称：

  Sulfonyloxyphenylurea compounds and herbicidal compositions

  摘要：

  新的苯磺酰氧基苯基脲，其化学式为##SPC1##其中R.sub.1为烷基，卤代烷基，苯基，至少一个取代烷基，卤代基和三氟甲基或二烷基氨基的苯基；R.sub.2为氢，1至4个碳原子的烷基或甲氧基。这些草甘膦是非常有效的除草剂，表现出特别选择性的作用。

  公开号：

  US03962306A1

文献信息

• US3962306A
  申请人：——

  公开号：US3962306A

  公开（公告）日：1976-06-08
• 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.
• Sulfonyloxyphenylurea compounds and herbicidal compositions
  申请人：Bayer Aktiengesellschaft

  公开号：US03962306A1

  公开（公告）日：1976-06-08

  New sulfonyloxyphenylureas of the formula ##SPC1## In which R.sub.1 is alkyl, haloalkyl, phenyl, phenyl substituted with at least one of alkyl, halo-substituted and trifluoromethyl or dialkylamino, and R.sub.2 is hydrogen, alkyl of from 1 to 4 carbon atoms, or methoxy Are outstandingly effective herbicides displaying particularly selective action.

  新的苯磺酰氧基苯基脲，其化学式为##SPC1##其中R.sub.1为烷基，卤代烷基，苯基，至少一个取代烷基，卤代基和三氟甲基或二烷基氨基的苯基；R.sub.2为氢，1至4个碳原子的烷基或甲氧基。这些草甘膦是非常有效的除草剂，表现出特别选择性的作用。