Hypofluorous acid

Hypofluorous acid is the chemical compound with the formula HOF. It is an intermediate in the oxidation of water by fluorine, which affords HF and oxygen. It is the only hypohalic acid that can be isolated as a solid. HOF is explosive, decomposing to oxygen and HF^[1].

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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 1.442 and 0.78 A, 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.

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

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, “The Crystal Structure of Hypofluorous Acid : Chain Formation by O-H^{. . .} O Hydrogen Bonds” Angewandte Chemie International Edition in English 1988, volume 27, pp 392-3.
2. ^ S. Rozen, M. Brand, Angew. Chem. Int. Ed. 1986, 25, 554-5; S. Dayan, Y. Bareket, S. Rozen, Tetrahedron 1999, 55, 3657.
3. ^ S. Rozen, S. Dayan, Angew. Chem. Int. Ed. 1999, 38, 3471-3.
4. ^ F. Linsker, R.L. Evans, J. Am. Chem. Soc. 1946, 68, 403.