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Hypofluorous acid
Hypofluorous acid
Hypochlorous acid
IUPAC name
Other names hydrogen hypofluorite
hydrogen fluorate(I)
fluoric(-I) acid
hydrogen monofluoroxygenate(0)
Identifiers
CAS number 14034-79-8
SMILES
Properties
Molecular formula HFO
Molar mass 36.0057 g mol−1
Appearance pale yellow liquid above −117 °C
white solid below −117 °C
Density  ? g/cm3, ?
Melting point

−117 °C (? K)

Boiling point

< 0 °C
decomposes at 0 °C

Solubility in water  ?
Related compounds
Other cations lithium hypofluorite, LiOF
Related compounds hypochlorous acid, HOCl
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Hypofluorous acid is the chemical compound with the formula HFO. It is an intermediate in the oxidation of water by fluorine, which produces hydrogen fluoride and oxygen. It is the only hypohalic acid that can be isolated as a solid. HOF is explosive, decomposing to oxygen and HF.[1] It was isolated in pure form by fluorination of ice.

The compound has been characterized in the solid phase by X-ray crystallography[1] as a bent molecule with an angle of 101°. The O-F and O-H bond lengths are 144.2 and 96.4 picometres, respectively. The solid framework consists of chains with O-H---O linkages. Note that these solid phase measurements differ somewhat from those observed in the gaseous phase, which are shown in the accompanying illustration.

For fluorine, the only known oxoacid is hypofluorous acid, HOF, in which fluorine is in the -1 oxidation state. It can be made by passing F2 gas over ice at -40 °C and collecting the HOF gas which condenses. It decomposes at room temperature to form HF and O

F2+ H2O------ HOF + HF

Hypofluorous acid in acetonitrile (generated in situ by passing gaseous fluorine through "wet" acetonitrile) serves as a highly electrophilic oxygen-transfer agent.[2][3] Treating phenanthroline with this reagent yielded the previously elusive 1,10-phenanthroline dioxide,[4] more than 50 years after the first unsuccessful attempt.[5]

See also

  • Hypochlorous acid, a related species that is more technologically important but has not been obtained in pure form.

References

  1. ^ a b W. Poll, G. Pawelke, D. Mootz, E. H. Appelman (1988). "The Crystal Structure of Hypofluorous Acid : Chain Formation by O-H · · · O Hydrogen Bonds". Angew. Chem. Int. Ed. Engl. 27: 392–3. doi:10.1002/anie.198803921.  
  2. ^ S. Rozen, M. Brand (1986). "Epoxidation of Olefins with Elemental Fluorine in Water/Acetonitrile Mixtures". Angew. Chem. Int. Ed. 25: 554–5. doi:10.1002/anie.198605541.  
  3. ^ S. Dayan, Y. Bareket, S. Rozen (1999). "An efficient α-hydroxylation of carbonyls using the HOF•CH3CN complex". Tetrahedron 55: 3657. doi:10.1016/S0040-4020(98)01173-9.  
  4. ^ S. Rozen, S. Dayan (1999). "At Last, 1,10-Phenanthroline-N,N′-dioxide, A New Type of Helicene, has been Synthesized using HOF⋅CH3CN". Angew. Chem. Int. Ed. 38: 3471–3. doi:10.1002/(SICI)1521-3773(19991203)38:23<3471::AID-ANIE3471>3.0.CO;2-O.  
  5. ^ F. Linsker, R.L. Evans (1946). "Phenanthroline Di-N-oxides". J. Am. Chem. Soc. 68: 403. doi:10.1021/ja01207a019.  
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