Preparation, NMR, and Ab Initio/IGLO/GIAO-MP2 Study of the Elusive Protonated Fluroformic Acid and Fluorocarbonyl Cation

Authors

  • Prof. Dr. George A. Olah,

    Corresponding author
    1. Loker Hydrocarbon Research Institute and Department of Chemistry University of Southern California University Park, Los Angels, CA 90089-1661 (USA) Fax: Int. code +(213)740-5087
    • Loker Hydrocarbon Research Institute and Department of Chemistry University of Southern California University Park, Los Angels, CA 90089-1661 (USA) Fax: Int. code +(213)740-5087
    Search for more papers by this author
  • Dr. Arwed Burrichter,

    1. Loker Hydrocarbon Research Institute and Department of Chemistry University of Southern California University Park, Los Angels, CA 90089-1661 (USA) Fax: Int. code +(213)740-5087
    Search for more papers by this author
  • Dr. Thomas Methew,

    1. Loker Hydrocarbon Research Institute and Department of Chemistry University of Southern California University Park, Los Angels, CA 90089-1661 (USA) Fax: Int. code +(213)740-5087
    Search for more papers by this author
  • Prof. Dr. Yashwant D. Vankar,

    1. Department of Chemistry Indian Institute of Technology Kanpur 208016 (India)
    Search for more papers by this author
  • Prof. Dr. Golam Rasul,

    1. Loker Hydrocarbon Research Institute and Department of Chemistry University of Southern California University Park, Los Angels, CA 90089-1661 (USA) Fax: Int. code +(213)740-5087
    Search for more papers by this author
  • Prof. Dr. G. K. Surya Prakash

    Corresponding author
    1. Loker Hydrocarbon Research Institute and Department of Chemistry University of Southern California University Park, Los Angels, CA 90089-1661 (USA) Fax: Int. code +(213)740-5087
    • Loker Hydrocarbon Research Institute and Department of Chemistry University of Southern California University Park, Los Angels, CA 90089-1661 (USA) Fax: Int. code +(213)740-5087
    Search for more papers by this author

  • Onium Ions Part 49. Support of our work by the National Science Foundation is gratefully appreciated. A. B. wishes to thank the Konrad-Adenauer-Foundation for a scholarship. Part 48: G. K. S. Prakash, Q. Wang, G. Rasul, G. A. Olah, J. Organomet. Chem., in press.

Abstract

original image

Protolysis of tert-butyl fluoroformate [Eq.(a)] in a solution of FSO3H/SbF5-SO2ClF at −78°C yields the stable protonated form of the elusive fluoroformic acid [FC(OH)2]+. It was characterized by 1H, 13C, and 19F NMR spectroscopy. Evidence was also obtained for the formation of fluorocarbonyl cation [FCO]+, but not for diprotonated fluororformic acid [FC(OH2)OH2]+.

Ancillary