(3-nitro-phenylsulfanyl)-acetic acid | 3996-40-5

• 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: (3-nitro-phenylsulfanyl)-acetic acid
• 英文别名: (3-Nitro-phenylmercapto)-essigsaeure；({3-Nitrophenyl}sulfanyl)acetic acid；2-(3-nitrophenyl)sulfanylacetic acid
• CAS: 3996-40-5
• 化学式: C₈H₇NO₄S
• 分子量: 213.214
• InChiKey: JEXWGRCQMMPHBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-nitro-phenylsulfanyl)-acetic acid 在 双氧水 、 溶剂黄146 作用下， 生成 3-Nitrophenylsulfonylessigsaeure
  参考文献：
  名称：

  Determination of Hammett ρ Values for Substituted Phenylmercapto-, Phenylsulfinyl-, and Phenylsulfonylacetic Acids

  摘要：

  DOI：

  10.1021/jo01019a043
• 作为产物：
  描述：

  3,3'-二硝基二苯二硫醚 在 sodium sulfide 、 sodium hydroxide 作用下， 生成 (3-nitro-phenylsulfanyl)-acetic acid
  参考文献：
  名称：

  Brand; Leyerzapf, Chemische Berichte, 1937, vol. 70, p. 284,296

  摘要：

  DOI：

文献信息

• Oxygenation of Substituted (Phenylthio)acetic Acids by Acidic Bromate: A Kinetic and Mechanistic Study and Validity of Linear Free-Energy Relationships
  作者：B. SURESH BABU、P. SUNITHA MANJARI、CH. SANJEEVA REDDY

  DOI：10.14233/ajchem.2022.23509

  日期：——

  Kinetics and mechanistic investigations on the oxygenation of (phenylthio)acetic acid and its substituted compounds using bromate in acid medium have been carried out. The reaction exhibited first-order in [bromate], 1.6 order in [H2SO4], less than one order in [substrate] and displayed solvent isotopic effect of 1.75 (kD2O/kH2O). The reaction rate is not affected by ionic strength variation, however

  对（苯硫基）乙酸及其取代化合物在酸性介质中使用溴酸盐的氧化反应进行了动力学和机理研究。该反应在[溴酸盐]中表现出一级，在[H2SO4]中表现出1.6级，在[底物]中表现出低于一级，并且显示出1.75（kD2O/kH2O）的溶剂同位素效应。反应速率不受离子强度变化的影响，但可以通过降低介质的介电常数来提高。底物芳基部分的结构修饰导致反应性发生变化，其中寻电子取代基降低了反应速率。研究的底物之间的反应性顺序为对甲氧基 > 对甲基 > -H > 对氯 ≈ 对溴 > 对硝基（苯硫基）乙酸，并且在速率常数和哈米特取代基常数（σ 值）之间显示出良好的相关性）。反应常数 (ρ) 值为负（303 K 时为-1.37），并且随着反应温度的升高而降低。所提出的机制涉及酸式溴酸盐和底物之间形成的复合物的分解。基于所提出的机制，推导了适当的利率法并测试了其有效性。激活参数和等速温度已经被评估和讨论。线性自由能关系的有效性已经被彻底讨论。
• Oxidative cleavage of S-arylmercaptoacetic acids by sodium perborate: Kinetic and correlation study
  作者：S. Kabilan、K. Pandiarajan、K. Krishnasamy、P. Sankar

  DOI：10.1002/kin.550270504

  日期：1995.5

  AbstractKinetics of oxidation of twenty six S‐arylmercaptoacetic acids (SAMA) (I) by sodium perborate (PB) have been studied in acid medium. The product of oxidation is the corresponding thiophenol. The rate data of meta‐and para‐substituted acids have been correlated with DSP equations. While the para‐compounds correlate well with σI and σR° values, the meta‐compounds correlate well with σI and σ values. The reaction constants are negative and of smaller magnitudes. Further, the ortho‐substituted acids show a good correlation with a triparametric equation involving Taft's σI and R° and Charton's steric parameter ν. There is a considerable steric contribution to the total ortho‐substituent effect. Based on these observations, mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed. © 1995 John Wiley & Sons, Inc.
• Oxidative cleavage of S-Arylmercaptoacetic acids by pyridinium chlorochromate: Kinetic and correlation analysis
  作者：S. Kabilan、R. Girija、V. Rajagopal

  DOI：10.1002/(sici)1097-4601(1999)31:10<683::aid-jck1>3.0.co;2-9

  日期：——

  Kinetics of oxidation of 24 S-Arylmercaptoacetic acids (SAMA) by pyridinium chlorochromate (PCC) have been studied in acidmedium. The product of oxidation is the corresponding thiophenol. The rate data of meta- and para-substituted acids have been correlated well with sigma(I), sigma(R)degrees values and the meta-compounds correlate well with F, R values. The reaction constants are negative and of smaller magnitudes. Further, the ortho-substituted acids show a good correlation with triparametric equation involving Taft's sigma(I) and sigma(R)degrees and charton's steric parameter nu. There is no considerable steric contribution to the total orthosubstituent effect. Based on these observations, the mechanism involving the formation of protonated arylsulfinylacetic acid intermediate, followed by an intramolecular rearrangement leading to the product thiophenol has been proposed. (C) 1999 John Wiley & Sons, Inc.
• NEW SYNTHESIS OF PHENYLTHIOGLYCOLIC ACIDS<i>via</i>RELATED TRIAZENE COMPOUNDS
  作者：Ali Disli、Yilmaz Yildirir

  DOI：10.1080/00304949809355295

  日期：1998.6
• Chou; Chi, Huaxue Xuebao/Acta Chimica Sinica, 1959, vol. 25, p. 38,39
  作者：Chou、Chi

  DOI：——

  日期：——