Hypofluorous Acid Information
Hypofluorous acid is the chemical compound with the formula HOF. 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. The structure has also been analyzed in the gas phase, a state in which the H—O—F bond angle is slightly narrower (97.2°).
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 O2
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 compound that is more technologically important but has not been obtained in pure form.
References
- ^ 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 (3): 392–3. doi:10.1002/anie.198803921.
- ^ S. Rozen, M. Brand (1986). "Epoxidation of Olefins with Elemental Fluorine in Water/Acetonitrile Mixtures". Angew. Chem. Int. Ed. 25 (6): 554–5. doi:10.1002/anie.198605541.
- ^ S. Dayan, Y. Bareket, S. Rozen (1999). "An efficient α-hydroxylation of carbonyls using the HOF·CH3CN complex". Tetrahedron 55 (12): 3657. doi:10.1016/S0040-4020(98)01173-9.
- ^ 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 (23): 3471–3. doi:10.1002/(SICI)1521-3773(19991203)38:23<3471::AID-ANIE3471>3.0.CO;2-O.
- ^ F. Linsker, R.L. Evans (1946). "Phenanthroline Di-N-oxides". J. Am. Chem. Soc. 68 (3): 403. doi:10.1021/ja01207a019.
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