S-(fluoroformyl)O-(trifluoroacetyl) thioperoxide, FC(O)S-OC(O)CF3: gas-phase structure and conformational properties

J Phys Chem A. 2006 Aug 31;110(34):10201-5. doi: 10.1021/jp0612984.

Abstract

The geometric structure and conformational properties of S-(fluoroformyl)O-(trifluoroacetyl) thioperoxide, FC(O)S-OC(O)CF3, were investigated by gas electron diffraction, matrix isolation infrared spectroscopy, and quantum chemical calculations (B3LYP with the 6-31G and aug-cc-pVTZ basis sets and MP2 with the 6-31G basis set). The experimental methods result in a mixture of two conformers with gauche conformation around the S-O bond. In the main conformer (82(7)% according to GED at 298 K), the C=O bond of the FC(O) group is oriented syn with respect to the S-O bond and phi(C-S-O-C) = 75(3) degrees . In the minor conformer (18(7)%), this C=O is oriented anti. Both conformers possess syn orientation of the C=O bond of the CF3C(O) group. The conformational properties and geometric parameters are reproduced reasonably well by the quantum chemical calculations, except for the S-O bond length, which is predicted too long by 0.04 A (B3LYP/aug-cc-pVTZ).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Electrons
  • Fluoroacetates*
  • Gases / chemistry
  • Hydrocarbons, Fluorinated / chemical synthesis
  • Hydrocarbons, Fluorinated / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Peroxides / chemical synthesis
  • Peroxides / chemistry*
  • Quantum Theory
  • Sensitivity and Specificity
  • Spectrophotometry, Infrared / methods
  • Trifluoroacetic Acid / chemical synthesis
  • Trifluoroacetic Acid / chemistry*

Substances

  • Fluoroacetates
  • Gases
  • Hydrocarbons, Fluorinated
  • Peroxides
  • S-(fluoroformyl)O-(trifluoroacetyl) thioperoxide
  • Trifluoroacetic Acid