trans-syn-s-trans-S-methyldithizone | 56677-22-6

• 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: trans-syn-s-trans-S-methyldithizone
• 英文别名: 3-methylthio-1,5-diphenylformazan；(E,E)-3-methylsulfanyl-1,5-diphenyl-formazan；(E,E)-3-Methylmercapto-1,5-diphenyl-formazan；3-MeS-1,5-Diphenylformazan；S-Methyl-dithizon；S-Methyldithizon
• CAS: 56677-22-6
• 化学式: C₁₄H₁₄N₄S
• 分子量: 270.358
• InChiKey: XGYMSSCEQNFPLH-MLHBKYQTSA-N

物化性质

• 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：

  trans-syn-s-trans-S-methyldithizone 以 氯仿 为溶剂， 生成 3-methylthio-1,5-diphenylformazan
  参考文献：
  名称：

  异构体3-甲硫基-1,5-二芳基甲醛的构型及其在溶液中的相互转化的X射线晶体学和光谱学研究

  摘要：

  1 H Nmr和ir光谱研究Ar.N：NC（SR）：N.NH.Ar（Ar = Ph， p- tolyl或o- tolyl; R = CH 3或CD 3）的溶液与纯异构体的X射线晶体结构使确定可见光谱随时间变化的结构原因成为可能。

  DOI：

  10.1039/c39800000763
• 作为产物：
  描述：

  3-methylthio-1,5-diphenylformazan 以 氯仿 为溶剂， 生成 trans-syn-s-trans-S-methyldithizone
  参考文献：
  名称：

  异构体3-甲硫基-1,5-二芳基甲醛的构型及其在溶液中的相互转化的X射线晶体学和光谱学研究

  摘要：

  1 H Nmr和ir光谱研究Ar.N：NC（SR）：N.NH.Ar（Ar = Ph， p- tolyl或o- tolyl; R = CH 3或CD 3）的溶液与纯异构体的X射线晶体结构使确定可见光谱随时间变化的结构原因成为可能。

  DOI：

  10.1039/c39800000763

文献信息

• Studies with dithizone. Part VI. S-alkyldithizones
  作者：H. Irving、C. F. Bell

  DOI：10.1039/jr9540004253

  日期：——
• Synthesis, DFT and kinetic studies of chromic S-methyldithizone
  作者：F.M.A. Muller、J. Conradie、K.G. von Eschwege

  DOI：10.1016/j.poly.2020.114386

  日期：2020.3

  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.
• HUTTON, A. T.;IRVING, H. M. N. H., J. CHEM. SOC. PERKIN TRANS., 1982, N 9, 1117-1121
  作者：HUTTON, A. T.、IRVING, H. M. N. H.

  DOI：——

  日期：——
• Hutton; Irving, Journal of the Chemical Society. Perkin transactions I, vol. II, p. 1982 1117
  作者：Hutton、Irving

  DOI：——

  日期：——
• Configuration-sensitive infrared bands and vibrational assignments of S-alkyldithizones based on isotopic substitutions
  作者：Osamu Yamada、Hidehumi Hiura、Takashi Igarashi、Norio Kaneko、Hiroaki Takahashi

  DOI：10.1016/0584-8539(88)80191-0

  日期：1988.1