- Hypofluorous acid
Chembox new
Name = Hypofluorous acid
ImageFile = Hypofluorous-acid-2D-dimensions.png
ImageFile1 = Hypofluorous-acid-3D-vdW.png
IUPACName = hypofluorous acid
OtherNames = hydrogen hypofluorite
hydrogen fluorate(I)
fluoric(I) acid
hydrogen monofluoroxygenate(0)| Section1 = Chembox Identifiers
SMILES = HOF
CASNo = 14034-79-8
RTECS =
Section2 = Chembox Properties
Formula = HFO
MolarMass = 36.0057 g mol−1
Appearance = pale yellow liquid above −117 °C
white solid below −117 °C
Density = ? g/cm3, ?
Solubility = ?
MeltingPt = −117 °C (? K)
BoilingPt =< 0 °C
decomposes at 0 °C
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards =
RPhrases =
SPhrases =
Section8 = Chembox Related
OtherCations =lithium hypofluorite , LiOF
OtherCpds =hypochlorous acid , HOClHypofluorous acid is the
chemical compound with the formula HOF. It is an intermediate in theoxidation ofwater byfluorine , which producesHF andoxygen . It is the only hypohalic acid that can be isolated as a solid. HOF is explosive, decomposing to oxygen and HF.cite journal | author = W. Poll, G. Pawelke, D. Mootz, E. H. Appelman | title = The Crystal Structure of Hypofluorous Acid : Chain Formation by O-H · · · O Hydrogen Bonds | journal =Angew. Chem. Int. Ed. Engl. | year = 1988 | volume = 27 | pages = 392–3 | doi = 10.1002/anie.198803921] It was isolated in pure form by fluorination of ice.The compound has been characterized in the solid phase by
X-ray crystallography 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 highlyelectrophilic oxygen-transfer agent. [cite journal | author = S. Rozen, M. Brand | journal =Angew. Chem. Int. Ed. | year = 1986 | volume = 25 | pages = 554–5 | doi = 10.1002/anie.198605541 | title = Epoxidation of Olefins with Elemental Fluorine in Water/Acetonitrile Mixtures] [cite journal | author = S. Dayan, Y. Bareket, S. Rozen | journal = Tetrahedron | year = 1999 | volume = 55 | pages = 3657 | doi = 10.1016/S0040-4020(98)01173-9 | title = An efficient α-hydroxylation of carbonyls using the HOF•CH3CN complex] Treatingphenanthroline with this reagent yielded the previously elusive "1,10-phenanthroline dioxide", [cite journal | author = S. Rozen, S. Dayan | journal =Angew. Chem. Int. Ed. | year = 1999 | volume = 38 | pages = 3471–3 | doi = 10.1002/(SICI)1521-3773(19991203)38:23<3471::AID-ANIE3471>3.0.CO;2-O | title = At Last, 1,10-Phenanthroline-N,N′-dioxide, A New Type of Helicene, has been Synthesized using HOF⋅CH3CN] more than 50 years after the first unsuccessful attempt. [cite journal | author = F. Linsker, R.L. Evans | journal =J. Am. Chem. Soc. | title = Phenanthroline Di-N-oxides | year = 1946 | volume = 68 | pages = 403 | doi = 10.1021/ja01207a019]ee also
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Hypochlorous acid , a related species that is more technologically important but has not been obtained in pure form.References
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