S-Methyl-dithizon | 6846-17-9

• 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: S-Methyl-dithizon
• 英文别名: Methyl N,2-diphenyldiazenecarbohydrazonothioate；methyl N'-anilino-N-phenyliminocarbamimidothioate
• CAS: 6846-17-9
• 化学式: C₁₄H₁₄N₄S
• 分子量: 270.358
• InChiKey: XGYMSSCEQNFPLH-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  399.8±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.11
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  氯化苯汞 、 S-Methyl-dithizon 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以94%的产率得到S-methyldithizonatophenylmercury(II)
  参考文献：
  名称：

  Synthesis, DFT and kinetic studies of chromic S-methyldithizone

  摘要：

  Dithizone is one of the most well-known trace-metal analysis reagents, however, its S-alkylated derivatives received very little attention up to date. Synthesis, kinetic studies of its photo- and chronochromic reactions, as well as DFT and TDDFT results are presented here. For comparitive purposes the corresponding phenylmercury complex was also synthesized and included in this study. Blue-shifts in lambda(max) of the S-methylated compounds are in excess of 60 nm as compared to the metal complex. Relative geometry optimized energies, atomic charge distribution in conjunction with H-1 NMR, as well as TDDFTs all point to the pink syn geometry of S-methyldithizone as the prevalent isomer, with the yellow anti geometry only of slightly higher (3.8 kJ/mol) energy. B3LYP provides significantly better UV-visible spectrum approximation than LC-BLYP, OLYP and PW91. At 20 degrees C the rate of the chronochromic reaction is 0.0073 s(-1) in chloroform, and that of the photochromic return reaction is 0.0023 s(-1) in ethanol. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2020.114386