trifluoromethyl-chlorocarbonyldisulfane | 27961-77-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: trifluoromethyl-chlorocarbonyldisulfane
• 英文别名: Chlorcarbonyl-trifluormethyl-disulfan；S-(trifluoromethylsulfanyl) chloromethanethioate
• CAS: 27961-77-9
• 化学式: C₂ClF₃OS₂
• 分子量: 196.602
• InChiKey: HHOFGQWTQNNDQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  120.4±45.0 °C(Predicted)
• 密度：
  1.718±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  trifluoromethyl-fluorocarbonyldisulfane 在 三氯化硼 作用下， 生成 trifluoromethyl-chlorocarbonyldisulfane
  参考文献：
  名称：

  Vibrational spectra and structures of halogencarbonyl alkyldisulfanes XC(O)SSR with X=F, Cl and R=CF3, CH3

  摘要：

  The disulfides FC(O)SSCF3, ClC(O)SSCF3 and ClC(O)SSCH3 have been prepared by new synthetic routes. Infrared and Raman spectra have been recorded and assigned. From the vibrational spectra and from the gas electron diffraction experiment it was concluded that FC(O)SSCF3 exists as a mixture of syn- and anti-conformers (C=O synperiplanar/antiperiplanar to S-S bond). The main conformer (83(5)% and DeltaG degrees = G degrees (anti) - G degrees (syn) = 0.95(28) kcal mol(-1)) possesses syn-structure. The vibrational spectra of the chlorocarbonyl disulfanes are interpreted in terms of a single conformer, but small amounts (<5%) of a second conformer cannot be excluded. Quantum chemical calculations (HF, MP2, B3PW91 with 6-31G* basis sets) reproduce the experimental results (conformational properties, geometric structure and vibrational frequencies) satisfactorily. The predicted difference in Gibbs free energy, DeltaG degrees, for FC(O)SSCF3 varies between 0.8 and 1.5 kcal mol(-1), those for the chlorine derivatives are larger than 2.6 kcal mol(-1). (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00515-2

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.SVol.2, 6.2.1.6.5, page 172 - 209
  作者：

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.1, 1.1.6.6, page 195 - 217
  作者：

  DOI：——

  日期：——
• Trifluoromethyldisulfane. A reactive nucleophile toward fluorinated acid halides
  作者：Craig A. Burton、Jean'ne M. Shreeve

  DOI：10.1021/ja00437a021

  日期：1976.10
• Haas, A.; Reinke, H.; Sommerhoff, J., Angewandte Chemie, 1970, vol. 9, p. 466 - 467
  作者：Haas, A.、Reinke, H.、Sommerhoff, J.

  DOI：——

  日期：——
• Vibrational spectra and structures of halogencarbonyl alkyldisulfanes XC(O)SSR with X=F, Cl and R=CF3, CH3
  作者：Angelika Hermann、Sonia E. Ulic、Carlos O. Della Védova、Hans-Georg Mack、Heinz Oberhammer

  DOI：10.1016/s0022-1139(01)00515-2

  日期：2001.12

  The disulfides FC(O)SSCF3, ClC(O)SSCF3 and ClC(O)SSCH3 have been prepared by new synthetic routes. Infrared and Raman spectra have been recorded and assigned. From the vibrational spectra and from the gas electron diffraction experiment it was concluded that FC(O)SSCF3 exists as a mixture of syn- and anti-conformers (C=O synperiplanar/antiperiplanar to S-S bond). The main conformer (83(5)% and DeltaG degrees = G degrees (anti) - G degrees (syn) = 0.95(28) kcal mol(-1)) possesses syn-structure. The vibrational spectra of the chlorocarbonyl disulfanes are interpreted in terms of a single conformer, but small amounts (<5%) of a second conformer cannot be excluded. Quantum chemical calculations (HF, MP2, B3PW91 with 6-31G* basis sets) reproduce the experimental results (conformational properties, geometric structure and vibrational frequencies) satisfactorily. The predicted difference in Gibbs free energy, DeltaG degrees, for FC(O)SSCF3 varies between 0.8 and 1.5 kcal mol(-1), those for the chlorine derivatives are larger than 2.6 kcal mol(-1). (C) 2001 Elsevier Science B.V. All rights reserved.