Sulfidosulfanylmethane | 97141-28-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 英文名称: Sulfidosulfanylmethane
• 英文别名: sulfidosulfanylmethane
• CAS: 97141-28-1
• 化学式: CH₃S₂
• 分子量: 79.1668
• InChiKey: KFLNNVFDKSNGBW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲硫醇 在 HOS^(1-) 作用下， 以 gas 为溶剂， 生成 Sulfidosulfanylmethane
  参考文献：
  名称：

  羟基硫化物阴离子HOS-的气相化学和热化学

  摘要：

  The chemistry and thermochemistry of the hydroxysulfide anion, HOS-, has been studied in a tandem flowing afterglow-selected ion flow tube (FA-SIFT). The reactions of HOS- with O2, CO, CO2, CS2, SO2, H2S, (CH3)3CSH, CH3SH, CH3Cl, and (CH3)2CHCl have been examined and compared to the corresponding reactions of HOO-. The gas-phase basicity of HOS- has been established via the bracketing technique [DELTAG(acid)0(HOSH) = 347 +/- 3 kcal mol-1, DELTAH(acid)0(HOSH) = 354 +/- 3.5 kcal mol-1]. Ab initio calculations have been carried out on HOS-, HSO-, HOSH, and H2SO which demonstrate that HOS- and HOSH are the more stable isomers. At the MP4SDTQ(FC)/6-311++G**//MP2(Full)/6-311++G** level of theory, these calculations predict DELTAH(acid)0(HOSH) = 356.7 kcal mol-1, in agreement with the experimentally determined value. Measurement of the forward and reverse rate constants for the reaction generating HOS- yields DELTAH(f)0 (HOS-) = -38.7 +/- 2 kcal mol-1, which when combined with the experimental electron affinity of HOS, determines DELTAH(f)0(HOS) = -0.5 +/- 2 kcal mol-1; this value is in good agreement with a recent ab initio determination. The gas-phase basicity of HSS-, the major product ion in the reaction of HOS- and CS2, has also been determined via the bracketing technique [DELTAG(acid)0(HSSH) = 339 +/- 3 kcal mol-1, DELTAH(acid)0(HSSH) = 346 +/- 3.5 kcal mol-1]. Combination of our gas-phase acidity values for HOSH and HSSH as well as for CH3SSH reported in a previous paper, with known electron affinities for the corresponding radicals, allows determination of the S-H bond dissociation energies (D298): HOSH (79 +/- 3.5 kcal mol-1), HSSH (76 +/- 3.5 kcal mol-1), and CH3SSH (79 +/- 3.5 kcal mol-1).

  DOI：

  10.1021/j100132a026

文献信息

• The Formation and Characterization of Three-Membered Ring Carbanions in the Gas Phase:  An Experimental and Theoretical Investigation of the Conjugate Bases of Thiirane, Thiirane <i>S</i>-Oxide, and Thiirane <i>S</i>,<i>S</i>-Dioxide
  作者：Grant N. Merrill、Uri Zoller、Dana R. Reed、Steven R. Kass

  DOI：10.1021/jo9906227

  日期：1999.10.1

  Deprotonation of thiirane, thiirane S-oxide, and thiirane S,S-dioxide was carried out in the gas phase, and the resulting anions were studied through a series of ion-molecule reactions. The cyclic conjugate bases of thiirane (Ib) and thiirane S,S-dioxide (3a) are formed whereas a facile ring opening isomerization to vinyl sulfenate anion (2d, CH2=CHSO-) is observed in the thiirane S-oxide case. Vinyl thiolate, the rearrangement product of the conjugate base of thiirane, also is obtained. Proton affinities were determined for Ib; 2d, and 3a. High-level ab initio calculations were also carried out, and the results compared with those obtained from experiment. Orbital arguments are advanced to explain the relative barriers to ring opening for the three anions of interest.
• Gas-phase chemistry and thermochemistry of the hydroxysulfide anion, HOS-
  作者：Richard A. J. O'Hair、Charles H. DePuy、Veronica M. Bierbaum

  DOI：10.1021/j100132a026

  日期：1993.7

  The chemistry and thermochemistry of the hydroxysulfide anion, HOS-, has been studied in a tandem flowing afterglow-selected ion flow tube (FA-SIFT). The reactions of HOS- with O2, CO, CO2, CS2, SO2, H2S, (CH3)3CSH, CH3SH, CH3Cl, and (CH3)2CHCl have been examined and compared to the corresponding reactions of HOO-. The gas-phase basicity of HOS- has been established via the bracketing technique [DELTAG(acid)0(HOSH) = 347 +/- 3 kcal mol-1, DELTAH(acid)0(HOSH) = 354 +/- 3.5 kcal mol-1]. Ab initio calculations have been carried out on HOS-, HSO-, HOSH, and H2SO which demonstrate that HOS- and HOSH are the more stable isomers. At the MP4SDTQ(FC)/6-311++G**//MP2(Full)/6-311++G** level of theory, these calculations predict DELTAH(acid)0(HOSH) = 356.7 kcal mol-1, in agreement with the experimentally determined value. Measurement of the forward and reverse rate constants for the reaction generating HOS- yields DELTAH(f)0 (HOS-) = -38.7 +/- 2 kcal mol-1, which when combined with the experimental electron affinity of HOS, determines DELTAH(f)0(HOS) = -0.5 +/- 2 kcal mol-1; this value is in good agreement with a recent ab initio determination. The gas-phase basicity of HSS-, the major product ion in the reaction of HOS- and CS2, has also been determined via the bracketing technique [DELTAG(acid)0(HSSH) = 339 +/- 3 kcal mol-1, DELTAH(acid)0(HSSH) = 346 +/- 3.5 kcal mol-1]. Combination of our gas-phase acidity values for HOSH and HSSH as well as for CH3SSH reported in a previous paper, with known electron affinities for the corresponding radicals, allows determination of the S-H bond dissociation energies (D298): HOSH (79 +/- 3.5 kcal mol-1), HSSH (76 +/- 3.5 kcal mol-1), and CH3SSH (79 +/- 3.5 kcal mol-1).