4,5-dithiomethyl-1,2-dithiole-3-thione | 72713-45-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5-dithiomethyl-1,2-dithiole-3-thione
• 英文别名: 4,5-dimercapto-1,2-dithiole-3-thione；4,5-Bis(methylsulfanyl)-3H-1,2-dithiole-3-thione；4,5-bis(methylsulfanyl)dithiole-3-thione
• CAS: 72713-45-2
• 化学式: C₅H₆S₅
• 分子量: 226.433
• InChiKey: MRMBLKOVSDIKFS-UHFFFAOYSA-N

物化性质

• 沸点：
  312.4±52.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-dithiomethyl-1,2-dithiole-3-thione 在 phosphites 作用下， 生成 dithietanne-1,3 diylidene bis(methylthio-2 dithioacetate de methyle)
  参考文献：
  名称：

  Polycarbon Disulfides SCnS (n = 1-3) and Their Protonated and Methylated Forms (HCnS2+ and CH3CnS2+): Tandem Mass Spectrometry and ab Initio MO Study

  摘要：

  Dissociative ionization of 4,5-bis(methylthio)-1,2-dithiole-3-thione (1) has allowed the detection of a series of carbon disulfide radical cations, SCnS.+ (n = 1-3), and their S-methylated forms, CH3SCnS+, in the gas phase of a mass spectrometer. The connectivities and stabilities of these ions and the corresponding neutrals have been probed by collisional activation (CA) and neutralization-reionization (NR) mass spectrometry. Moreover, the sites of protonation and cationic methylation of the polycarbon disulfides have been investigated by a combination of flash vacuum pyrolysis, chemical ionization, and CAMS (FVP/CI/MS/MS). The experimental results are supported by ab initio MO calculations at the QCISD(T)/6-311+G(2d,p) + ZPVE level. Both experiments and calculations indicate that the most favorable site of protonation and methylation is the carbon atom for C2S2 and C3S2 but a sulfur atom for CS2. The proton affinities (298 K) of C2S2 and C3S2 are predicted to be 842 and 818 kJ mol(-1), respectively.

  DOI：

  10.1021/j100046a010
• 作为产物：
  描述：

  4,5-双(苄基硫代)-1,2-二硫醇-3-硫醇 、 碘甲烷 在 ammonium acetate 、 sodium methylate 作用下， 生成 4,5-dithiomethyl-1,2-dithiole-3-thione
  参考文献：
  名称：

  Steimecke, Guenter; Sieler, Hans-Joachim; Kirmse, Reinhard, Phosphorus and Sulfur and the Related Elements, 1981, vol. 12, p. 237 - 248

  摘要：

  DOI：

文献信息

• Photopolymerization of Liquid Carbon Disulfide Produces Nanoscale Polythiene Films
  作者：Peter B. Zmolek、Honglae Sohn、Peter K. Gantzel、William C. Trogler

  DOI：10.1021/ja003200j

  日期：2001.2.1

  stoichiometry (CS(n))(x). The polymer, from here on called (CS)(x), forms as a approximately 200 nm thick transparent golden membrane as measured by SEM and AFM techniques. IR spectra for this polymer show some similarities with those obtained for the gas-phase photopolymerized (CS(2))(x) and the high-pressure-phase polymer of CS(2), called Bridgman's Black. The observed FT-IR absorptions of (CS)(x) include prominent

  液相二硫化碳的宽带太阳能或 300--400 nm 辐射（Hg--Xe 弧源）产生一种新的碳-硫聚合物，其化学计量约为 (n = 1.04--1.05) (CS(n)) （X）。根据 SEM 和 AFM 技术测量，此后称为 (CS)(x) 的聚合物形成约 200 nm 厚的透明金色膜。这种聚合物的 IR 光谱显示出与气相光聚合 (CS(2))(x) 和 CS(2) 的高压相聚合物（称为 Bridgman's Black）获得的那些相似。观察到的 (CS)(x) 的 FT-IR 吸收包括在 1431 (s, br)、1298 (m)、1250 (ms) 和 1070 cm(-1) (m) 处的突出特征。与之前的 (CS(2))(x) 提案相比，(13)α-(C(3)S(5))R(2) 和 β-(C(3)S(5))R(2)（R = 甲基或苯甲酰基）的 C 标记和模型化合物研究表明在 1431 cm(-1)
• Synthesis and X-ray structure of a novel 1,2,4-trithiolane
  作者：Martin R. Bryce、Alexander K. Lay、Andrei S. Batsanov、Judith A. K. Howard

  DOI：10.1002/jhet.5570360341

  日期：1999.5

  Photolysis of 1,2-dithiole-3-thione derivative 1 results in the formation of the 1,2,4-trithiolane derivative 2, the structure of which was established by single crystal X-ray analysis. Interesting bond delocalisation is observed in the molecular structure. A mechanism involving dimerisation of 1 followed by loss of sulfur is proposed.

  1,2-二硫代-3-硫酮衍生物1的光解导致1,2,4-三硫杂环戊烷衍生物2的形成，其结构是通过单晶X射线分析确定的。在分子结构中观察到有趣的键离域。提出了一种涉及二聚化1，然后损失硫的机理。
• Synthesis and stereochemistry of bis(dithiacrown ether) and dodecylthio substituted (E)-thiodesaurines
  作者：Sandra Rudershausen、Hans-Joachim Drexler、Hans-J�rgen Holdt

  DOI：10.1002/prac.19983400507

  日期：——

  Reductive dimerization of dodecylthio substituted 1,2-dithiole-3-thiones 6a-b and trithion-dithiacrown ethers 10a-c with triethyl phosphite furnished bis- and tetrakis (dodecylthio), and bis(dithiacrown ether) substituted thiodesaurines (E)-11a-b and (E)-12a-c. The stereochemistry of bis(dithia[15]crown-5)-thiodesaurine (E)-12b has been determined by X-ray crystallographic analysis.
• Gionis, Vassilis; Fichet, Odile; Izumi, Mitsuru, Chemistry Letters, 1991, # 5, p. 871 - 874
  作者：Gionis, Vassilis、Fichet, Odile、Izumi, Mitsuru、Garrigou-Lagrange, Chantal、Amiell, Jacques、et al.

  DOI：——

  日期：——
• Amzil, Jamal; Catel, Jean-Marie; Le Coustumer, Gerard, Bulletin de la Societe Chimique de France, 1988, # 1, p. 101 - 105
  作者：Amzil, Jamal、Catel, Jean-Marie、Le Coustumer, Gerard、Mollier, Yves、Sauve, Jean-Pierre

  DOI：——

  日期：——