Hypofluorous acid: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 413938817

| Name = Hypofluorous acid

| ImageFile = Hypofluorous-acid-2D-dimensions.png

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| ImageName = Hypofluorous acid

| ImageFile1 = Hypofluorous-acid-3D-vdW.png

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| ImageName1 = Hypochlorous acid

| IUPACName = hypofluorous acid

| OtherNames = hydrogen hypofluorite<br />hydrogen fluorate(I)<br />fluoric(-I) acid <br />hydrogen monofluoroxygenate(0)| Section1 = {{Chembox Identifiers

| SMILES = HOF

| CASNo = 14034-79-8

| RTECS =

}}

| Section2 = {{Chembox Properties

| Formula = HOF

| MolarMass = 36.0057 g mol⁻¹

| Appearance = pale yellow liquid above −117 °C<br />white solid below −117 °C

| Density = ? g/cm³, ?

| Solubility = ?

| MeltingPt = −117 °C (? K)

| BoilingPt =< 0 °C<br />decomposes at 0 °C

}}

| Section7 = {{Chembox Hazards

| ExternalMSDS =

| MainHazards =

| RPhrases =

| SPhrases =

}}

| Section8 = {{Chembox Related

| OtherCations = [[lithium hypofluorite]], LiOF

| OtherCpds = [[hypochlorous acid]], HOCl

}}

'''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.<ref name="Poll">{{cite journal | author = W. Poll, G. Pawelke, D. Mootz, E. H. Appelman | title = The Crystal Structure of Hypofluorous Acid : Chain Formation by O-H &middot; &middot; &middot; O Hydrogen Bonds | journal = [[Angew. Chem. Int. Ed. Engl.]] | year = 1988 | volume = 27 | issue = 3 | pages = 392–3 | doi = 10.1002/anie.198803921}}</ref> It was isolated in pure form by fluorination of ice.

The compound has been characterized in the solid phase by [[X-ray crystallography]]<ref name="Poll"/> 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.<ref>{{cite journal | author = S. Rozen, M. Brand | journal = [[Angew. Chem. Int. Ed.]] | year = 1986 | volume = 25 | issue = 6 | pages = 554–5 | doi = 10.1002/anie.198605541 | title = Epoxidation of Olefins with Elemental Fluorine in Water/Acetonitrile Mixtures}}</ref><ref>{{cite journal | author = S. Dayan, Y. Bareket, S. Rozen | journal = [[Tetrahedron (journal)|Tetrahedron]] | year = 1999 | volume = 55 | issue = 12 | pages = 3657 | doi = 10.1016/S0040-4020(98)01173-9 | title = An efficient α-hydroxylation of carbonyls using the HOF•CH3CN complex}}</ref> Treating [[phenanthroline]] with this reagent yielded the previously elusive ''1,10-phenanthroline dioxide'',<ref>{{cite journal | author = S. Rozen, S. Dayan | journal = [[Angew. Chem. Int. Ed.]] | year = 1999 | volume = 38 | issue = 23 | 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}}</ref> more than 50 years after the first unsuccessful attempt.<ref>{{cite journal | author = F. Linsker, R.L. Evans | journal = [[J. Am. Chem. Soc.]] | title = Phenanthroline Di-N-oxides | year = 1946 | volume = 68 | issue = 3 | pages = 403 | doi = 10.1021/ja01207a019}}</ref>

[[Category:Acids]]

[[cs:Kyselina fluorná]]

[[de:Hypofluorige Säure]]

[[fr:Acide hypofluoreux]]

[[ko:하이포플루오르산]]

[[it:Acido ipofluoroso]]

[[nl:Waterstofhypofluoriet]]

[[ja:次亜フッ素酸]]

[[sv:Hypofluoritsyra]]

[[zh:次氟酸]]