Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: the first nonsymmetric acyl trioxide.

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  • Author(s): Manetti MD;Manetti MD; Burgos Paci MA; Argüello GA
  • Source:
    The journal of physical chemistry. A [J Phys Chem A] 2009 Jul 30; Vol. 113 (30), pp. 8523-8.
  • Publication Type:
    Journal Article; Research Support, Non-U.S. Gov't
  • Language:
    English
  • Additional Information
    • Source:
      Publisher: American Chemical Society Country of Publication: United States NLM ID: 9890903 Publication Model: Print Cited Medium: Internet ISSN: 1520-5215 (Electronic) Linking ISSN: 10895639 NLM ISO Abbreviation: J Phys Chem A Subsets: MEDLINE
    • Publication Information:
      Original Publication: Washington, D.C. : American Chemical Society, c1997-
    • Subject Terms:
      Carbonates/*chemistry ; Hydrocarbons, Fluorinated/*chemistry ; Oxides/*chemistry; Carbonates/chemical synthesis ; Computer Simulation ; Hydrocarbons, Fluorinated/chemical synthesis ; Models, Chemical ; Oxides/chemical synthesis ; Spectrophotometry, Infrared ; Temperature
    • Abstract:
      This paper reports for the first time the synthesis and characterization of trifluoromethyl fluoroformyl trioxicarbonate, CF(3)OC(O)OOOC(O)F. The new trioxide is obtained from the gas-phase photolytic reaction of CF(3)C(O)OC(O)CF(3) and FC(O)C(O)F at 223-228 K. It is a very thermally labile molecule that decomposes at room temperature by rupture of either of the CF(3)OC(O)O-O-OC(O)F bonds. These bonds are nonequivalent, and a branching ratio of 0.8 for fragmentation through the CF(3)OC(O)OO-OC(O)F bond was obtained. Unambiguous identification was possible through reaction of the trioxide with an excess of NO(2). Potential-energy surfaces (PES) of the different rotamers were studied by the B3LYP/6-311+G* method, and analysis of the IR frequency of the possible mixture of rotamers agrees excellently with the experimental IR spectrum. This molecule is the first nonsymmetric acyl trioxide reported in the literature.
    • Accession Number:
      0 (Carbonates)
      0 (Hydrocarbons, Fluorinated)
      0 (Oxides)
      0 (trifluoromethyl fluoroformyl trioxicarbonate)
    • Publication Date:
      Date Created: 20090902 Date Completed: 20091209 Latest Revision: 20090901
    • Publication Date:
      20240829
    • Accession Number:
      10.1021/jp9022772
    • Accession Number:
      19719309