The synthesis of FC(O)OONO2 is accomplished
by the photolysis of a mixture of (FCO)2, NO2,
and O2. The
pure product is isolated after trap-to-trap condensation and the
removal of byproducts by treatment of the crude
product with O3 and AsF5. The colorless
liquid freezes at −105 °C; its boiling point is 32 °C. At 20
°C and a
few millibars, FC(O)OONO2 decomposes in the gas
phase with a half-life of 20 h. FC(O)OONO2
is characterized
by vapor pressure measurements, vibrational, 19F NMR,
13C NMR and UV spectroscopies as well as by
mass
spectrometry. According to the vibrational and NMR spectra, the
compound exists at room temperature only as
a syn conformer. The molecular structure of
FC(O)OONO2 is determined by gas electron
diffraction. The molecule
possesses a skew structure with a dihedral angle of φ(COON) =
86.2(14)°. The short O−O bond (1.420(6)
Å)
and the long N−O bond (1.514(6) Å) are consistent with the
chemical properties of this compound. The
experimental geometry is reproduced reasonably well by quantum
chemical.
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