2-[(3-Chlorophenyl)sulfanyl]-3,5-dinitropyridine | 192825-41-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(3-Chlorophenyl)sulfanyl]-3,5-dinitropyridine
• 英文别名: 2-(3-chlorophenyl)sulfanyl-3,5-dinitropyridine
• CAS: 192825-41-5
• 化学式: C₁₁H₆ClN₃O₄S
• 分子量: 311.705
• InChiKey: QNWXOIMAUOCDTI-UHFFFAOYSA-N

物化性质

• 沸点：
  460.8±45.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(3-Chlorophenyl)sulfanyl]-3,5-dinitropyridine 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 3,3’-二氯二苯二硫醚 、 2-羟基-3,5-二硝基吡啶
  参考文献：
  名称：

  Fathalla, Magda F.; Ibrahim, Mahmoud F.; Hamed, Ezzat A., Journal of Chemical Research, 2004, # 2, p. 150 - 151

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯苯硫酚 、 2-氯-3,5-二硝基吡啶 在 sodium 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以85%的产率得到2-[(3-Chlorophenyl)sulfanyl]-3,5-dinitropyridine
  参考文献：
  名称：

  Nucleophilic substitution at the pyridine ring. Kinetics of the reaction of 2-chloro-3,5-dinitropyridine with arylthiolates in methanol

  摘要：

  The reaction rates of 2-chloro-3,5-dinitropyridine 1 with a series of arylthiolates 2a-h in methanol have been measured at 25 degrees C. The products are the corresponding 2-thioaryl-3,5-dinitropyridine 3a-h. Good Hammett correlation with rho Value -1.19 was obtained suggesting an elimination-addition mechanism SNAr and the formation of Meisenheimer-like intermediates. Plot of log k(2) vs. pK(a) values of arylthiols gave straight line with beta = 0.38 indicating that the Ti-bond breaking in the pyridine ring is so much advanced over bond making between the nucleophile and the carbon that bears the chlorine atom. Excellent correlation between log k(2) and log K (carbon basicity of arylthiolates) was obtained. (C) 1997 John Wiley & Sons. Inc.

  DOI：

  10.1002/(sici)1097-4601(1997)29:7<515::aid-kin5>3.0.co;2-x

文献信息

• Fathalla, Magda F.; Ibrahim, Mahmoud F.; Hamed, Ezzat A., Journal of Chemical Research, 2004, # 2, p. 150 - 151
  作者：Fathalla, Magda F.、Ibrahim, Mahmoud F.、Hamed, Ezzat A.

  DOI：——

  日期：——
• Nucleophilic substitution at the pyridine ring. Kinetics of the reaction of 2-chloro-3,5-dinitropyridine with arylthiolates in methanol
  作者：Ezzat A. Hamed

  DOI：10.1002/(sici)1097-4601(1997)29:7<515::aid-kin5>3.0.co;2-x

  日期：——

  The reaction rates of 2-chloro-3,5-dinitropyridine 1 with a series of arylthiolates 2a-h in methanol have been measured at 25 degrees C. The products are the corresponding 2-thioaryl-3,5-dinitropyridine 3a-h. Good Hammett correlation with rho Value -1.19 was obtained suggesting an elimination-addition mechanism SNAr and the formation of Meisenheimer-like intermediates. Plot of log k(2) vs. pK(a) values of arylthiols gave straight line with beta = 0.38 indicating that the Ti-bond breaking in the pyridine ring is so much advanced over bond making between the nucleophile and the carbon that bears the chlorine atom. Excellent correlation between log k(2) and log K (carbon basicity of arylthiolates) was obtained. (C) 1997 John Wiley & Sons. Inc.