ethylxanthogenate | 28563-38-4

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: ethylxanthogenate
• 英文别名: O-ethyl dithiocarbonate；O-ethyl xanthate ion；ethyl xanthate anion；ethylxanthate anion；ethyl xanthate；Aethylxanthogenat；Carbonodithioic acid, O-ethyl ester；ethoxymethanedithioate
• CAS: 28563-38-4
• 化学式: C₃H₅OS₂
• 分子量: 121.204
• InChiKey: ZOOODBUHSVUZEM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethylxanthogenate 在 sodium nitrate 、 C₈MoN₈^(3-)*3Na⁽¹⁺⁾ 作用下， 以 水 、 丙酮 为溶剂， 生成 二黄原酸
  参考文献：
  名称：

  Nichols, Peter J.; Grant, Michael W., Australian Journal of Chemistry, 1989, vol. 42, # 7, p. 1085 - 1102

  摘要：

  DOI：
• 作为产物：
  描述：

  二黄原酸 在 sodium nitrate 、 C₈MoN₈^(3-)*3Na⁽¹⁺⁾ 作用下， 以 水 、 丙酮 为溶剂， 生成 ethylxanthogenate
  参考文献：
  名称：

  Nichols, Peter J.; Grant, Michael W., Australian Journal of Chemistry, 1989, vol. 42, # 7, p. 1085 - 1102

  摘要：

  DOI：

文献信息

• Radical chemistry of thiohydroxamic acid esters
  作者：Derek H.R. Barton、Gerhard Kretzschmar

  DOI：10.1016/s0040-4039(00)94229-1

  日期：1983.1

  Thiohydroxamic esters in general decompose smoothly by a radical chain reaction to give carbon radicals which can be quenched in a synthetically useful manner.

  硫代异羟肟酸酯通常通过自由基链反应平稳地分解以产生碳原子团，其可以以合成上有用的方式被淬灭。
• A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles
  作者：Lei Zhu、Mingbao Zhang、Miao Dai

  DOI：10.1002/jhet.5570420440

  日期：2005.5

  A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles is described. The key feature of the synthesis is an exclusive ortho-selective nucleophilic aromatic substitution reaction of ortho-haloanilines with potassium/sodium O-ethyl dithiocarbonate under mild conditions. Subsequent intra-molecular cycliza-tion affords 2-mercaptobenzothiazoles in high yields. The 2-mercaptobenzothiazoles are readily

  描述了2-巯基和2-氯苯并噻唑的方便合成。合成的关键特征是在温和条件下邻卤代苯胺与钾/ O-乙基二硫代碳酸氢钠的独家邻位选择性亲核芳族取代反应。随后的分子内环化以高收率提供2-巯基苯并噻唑。用硫酰氯处理后，2-巯基苯并噻唑容易转化为相应的2-氯苯并噻唑。
• Synthesis, structure and electrochemical behaviour of octahedral nickel(II) complexes with one 1,1-dithio and one macrocyclic ligand
  作者：R. Vicente、A. Escuer、J. Ribas、A. Dei、X. Solans、T. Calvet

  DOI：10.1016/s0277-5387(00)83979-0

  日期：——

  the same ligands except Tac and Ac, are described. The structure of [Ni( DL -CTH) (Et 2 Dtc)](ClO 4 ) is also reported. This complex crystallizes in the monoclinic space group P 2 1 / a with cell parameters a = 19.551(4), b = 13.446(3), c = 11.428(3) A, β = 95.54(3)° and Z = 4. The isolated [Ni( DL -CTH)(Et 2 Dtc)] + cation shows a distorted cis -octahedral coordination around the nickel(II) ion. The

  摘要[Ni（DL -CTH）L]（ClO 4）和[Ni（Cy）L']（ClO 4）的合成及电化学行为，其中DL -CTH为5,5,7,12的外消旋异构体，12,14-六甲基-1,4,8,11-四氮杂环十四烷，Cy为1,4,8,11-四氮杂环十四烷（Cyclam），L为二甲基二硫代氨基甲酸酯（Me 2 Dtc），二乙基二硫代氨基甲酸酯（Et 2 Dtc），吡咯烷基二硫代氨基甲酸酯（描述了PyrrDtc，黄原酸乙酯（Etxant），硫代乙酸酯（Tac）和乙酸酯（Ac）和L'是相同的配体，除了Tac和Ac。还报道了[Ni（DL -CTH）（Et 2 Dtc）]（ClO 4）的结构。该配合物在单斜空间群P 2 1 / a中结晶，其单元参数为a = 19.551（4），b = 13.446（3），c = 11.428（3）A，β= 95.54（3）°和Z = 4。分离的[Ni（DL -CTH）（Et
• Reactions of carbonyl and nitrosyl ruthenium complexes with uninegative (X,S)-donor ligands (X = S, P)
  作者：A. Gutierrez-Alonso、L. Ballester-Reventos

  DOI：10.1016/s0277-5387(00)81364-9

  日期：1991.1

  Reactions of 1,1-dithiolates (EtOCS2− and Et2NCS2−) and the related (P,S)- donor ligand (Ph2PCSNPh−) with halocarbonylphosphine complexes of ruthenium give halide substitution derivatives with chelation of the (S,S)- or (P,S)-donor ligand. The reaction of [RuCl2(CO)(CS)(PPh3)2] with dithiolates gives rise to displacement of the thiocarbonyl ligand, while with Ph2PCSNPh− the derivative [RuCl(Ph2PCSNPh)(CO)

  1,1- dithiolates反应（EtOCS 2 -和Et 2 NCS 2 - ）和相关的（P，S） -供体配体（PH 2 PCSNPh - ）与halocarbonylphosphine的钌给予卤化物取代衍生物与螯合络合物（S （S）-或（P，S）-供体配体。的反应将[RuCl 2（CO）（CS）（PPH 3）2与dithiolates]产生了硫代羰基配体的位移，而的Ph 2 PCSNPh -的衍生物将[RuCl（PH 2 PCSNPh）（CO）（CS） （PPh 3）]。羰基亚硝酰基络合物[RuCl（CO）（NO）（PPh 3）2 ]与亚硝酰基的置换反应并形成[RuCl（X，S）（CO）（PPh 3）2 ]络合物。
• Kinetics and mechanism of the oxidation of ethyl xanthate and ethyl thiocarbonate by hydrogen peroxide
  作者：Ewen Silvester、David Truccolo、Fu Ping Hao

  DOI：10.1039/b204222c

  日期：2002.8.27

  Kinetic studies on the oxidation of ethyl xanthate (O-ethyl dithiocarbonate) by hydrogen peroxide have been conducted for a range of ethyl xanthate and hydrogen peroxide concentrations over the pH range 8–12. The initial reaction product is a canonical form of O-ethyl S-oxodithiocarbonate. Further oxidation leads to a bifurcation in the reaction pathway, with the formation of either O-ethyl thiocarbonate or a canonical form of O-ethyl S-oxoperoxydithiocarbonate. The partitioning of the reaction between these alternative reaction paths is pH dependent, with the proportion directed towards the O-ethyl thiocarbonate branch increasing over the pH range 10 to12. Further oxidation of O-ethyl thiocarbonate leads to the formation of O-ethyl S-oxothiocarbonate (or a canonical form thereof), analogous to the initial oxygen addition to ethyl xanthate. For both reaction branches the ultimate sulfur-containing product is sulfate. Apart from the process controlling the bifurcation, the reaction kinetics can be modelled as a series of bimolecular oxygen addition steps. This kinetic model is supported by hydroxyl radical scavenging experiments (using tert-butyl alcohol) that suggest no involvement by OH˙. The pH dependence of the rate parameters indicates that reaction occurs exclusively with H2O2 rather than HO2−, consistent with the expected nucleophilic attack at the peroxide oxygen. The process controlling the partitioning between the two alternative pathways is proposed to originate from an oxygen addition adduct of O-ethyl S-oxodithiocarbonate. This work reveals that a range of potential metal ion complexants may be produced in the industrial application of xanthates (primarily sulfide mineral extraction, but also including viscose rayon production and pesticide manufacture), and that the environmental chemistry of these reagents is more complex than has been previously appreciated.

  对过氧化氢氧化黄原酸乙酯（O-乙基二硫代碳酸酯）的动力学进行了研究，黄原酸乙酯和过氧化氢的浓度范围在 pH 值 8-12 之间。最初的反应产物是 S-氧代二硫代碳酸 O-乙基酯的典型形式。进一步氧化会导致反应途径分叉，形成硫代碳酸 O-乙基酯或 S-氧代过氧化二硫代碳酸 O-乙基酯的典型形式。反应在这些替代反应途径之间的分配取决于 pH 值，在 pH 值为 10 到 12 的范围内，生成 O-乙基硫代碳酸酯分支的比例会增加。硫代碳酸 O-乙基酯的进一步氧化会形成硫代碳酸 S-氧 O-乙基酯（或其典型形式），类似于黄原酸乙酯的初始加氧反应。这两个反应分支的最终含硫产物都是硫酸盐。除了控制分叉的过程外，反应动力学可模拟为一系列双分子加氧步骤。羟基自由基清除实验（使用叔丁醇）支持这一动力学模型，实验表明羟基自由基不参与反应。速率参数的 pH 依赖性表明，反应只与 H2O2 而不是 HO2- 发生，这与预期的过氧氧亲核攻击一致。据推测，控制两种替代途径之间分配的过程源于 O-ethyl S-oxodithiocarbonate 的氧加成加合物。这项研究揭示了黄原酸盐在工业应用（主要是硫化物矿物提取，也包括粘胶人造丝生产和杀虫剂制造）中可能产生的一系列潜在金属离子络合剂，以及这些试剂的环境化学性质比以往认识到的更为复杂。