| Revision as of 14:51, 9 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipe← Previous edit |
Latest revision as of 13:29, 13 December 2024 edit undoDMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,474 edits Removing from Category:Oxoacids using Cat-a-lot |
| (127 intermediate revisions by 67 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
| Watchedfields = changed |
|
|Verifiedfields=changed |
|
|
|Watchedfields=changed |
|
| verifiedrevid = 413938817 |
|
|
|
|verifiedrevid=428256114 |
|
| Name = Hypofluorous acid |
|
|
| ImageFile = Hypofluorous-acid-2D-dimensions.png |
|
|Name=Hypofluorous acid |
|
|
|ImageFile=Hypofluorous-acid-2D-dimensions.png |
|
|
|ImageName=Hypofluorous acid |
|
<!-- | ImageSize = 160px --> |
|
|
|
|ImageCaption=Gas-phase structure |
|
| ImageName = Hypofluorous acid |
|
|
| ImageFile1 = Hypofluorous-acid-3D-vdW.png |
|
|ImageFile1=Hypofluorous-acid-3D-vdW.png |
|
|
|ImageName1=Hypofluorous acid |
|
<!-- | ImageSize1 = 130px --> |
|
|
|
|ImageCaption1={{legend|white|], H}}{{legend|red|], O}}{{legend|rgb(211, 232, 81)|], F}} |
|
| ImageName1 = Hypochlorous acid |
|
|
| IUPACName = hypofluorous acid |
|
|IUPACName=Hypofluorous acid |
|
| OtherNames = hydrogen hypofluorite<br />hydrogen fluorate(I)<br />fluoric(-I) acid <br />hydrogen monofluoroxygenate(0)| Section1 = {{Chembox Identifiers |
|
|OtherNames={{ubl|Fluoranol|Fluoric(-I) acid|Hydrogen hypofluorite|Hydrogen fluorate(-I)|Hydrogen monofluoroxygenate(0)|Hydroxyl fluoride}} |
|
|
|Section1={{Chembox Identifiers |
|
| SMILES = HOF |
|
|
| CASNo = 14034-79-8 |
|
| SMILES = OF |
|
|
| CASNo_Ref = {{cascite|correct|??}} |
|
| RTECS = |
|
|
|
| CASNo = 14034-79-8 |
|
}} |
|
|
|
| PubChem = 123334 |
|
| Section2 = {{Chembox Properties |
|
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
| Formula = HOF |
|
|
|
| ChemSpiderID = 109936 |
|
| MolarMass = 36.0057 g mol<sup>−1</sup> |
|
|
|
| InChI = 1/FHO/c1-2/h2H |
|
| Appearance = pale yellow liquid above −117 °C<br />white solid below −117 °C |
|
|
|
| InChIKey = AQYSYJUIMQTRMV-UHFFFAOYAN |
|
| Density = ? g/cm<sup>3</sup>, ? |
|
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
| Solubility = ? |
|
|
|
| StdInChI = 1S/FHO/c1-2/h2H |
|
| MeltingPt = −117 °C (? K) |
|
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
| BoilingPt =< 0 °C<br />decomposes at 0 °C |
|
|
|
| StdInChIKey = AQYSYJUIMQTRMV-UHFFFAOYSA-N |
|
}} |
|
|
|
| RTECS = |
|
| Section7 = {{Chembox Hazards |
|
|
|
}} |
|
| ExternalMSDS = |
|
|
|
|Section2={{Chembox Properties |
|
| MainHazards = |
|
|
|
| Formula = HOF |
|
| RPhrases = |
|
|
|
| MolarMass = 36.0057 g/mol |
|
| SPhrases = |
|
|
|
| Appearance = pale yellow liquid above −117 °C<br />white solid below −117 °C |
|
}} |
|
|
|
| Density = |
|
| Section8 = {{Chembox Related |
|
|
|
| Solubility = |
|
| OtherCations = ], LiOF |
|
|
|
| MeltingPtC = −117 |
|
| OtherCpds = ], HOCl |
|
|
|
| BoilingPt = decomposes at {{cvt|0|C|F K}}{{citation needed|date=July 2019}} |
|
}} |
|
|
|
}} |
|
|
|Section3={{Chembox Structure |
|
|
| PointGroup = C<sub>s</sub> |
|
}} |
|
}} |
|
|
|Section7={{Chembox Hazards |
|
|
| NFPA-H = 4 |
|
|
| NFPA-F = 0 |
|
|
| NFPA-R = 4 |
|
|
| NFPA-S = OX |
|
|
| ExternalSDS = |
|
|
| MainHazards = Explosive, strong oxidizer, corrosive |
|
|
}} |
|
|
|Section9={{Chembox Related |
|
|
| OtherCations = ] |
|
|
| OtherCompounds = {{ubl|]|]|]|]|]|]|]|]|]|]|]|]|]}} |
|
|
}}}} |
|
|
'''Hypofluorous acid''', ] {{chem2|HOF|auto=1}}, is the only known ] of fluorine and the only known oxoacid in which the main atom gains electrons from ] to create a negative oxidation state. The ] of the oxygen in this acid (and in the hypofluorite ion {{chem2|OF−}} and in its ] called hypofluorites) is 0, while its ] is 2. It is also the only ] that can be isolated as a ]. HOF is an ] in the ] of ] by ], which produces ], ], ], ] and ]. HOF is explosive at room temperature, forming HF and {{chem2|O2}}:<ref name="Poll">{{cite journal |author1=W. Poll |author2=G. Pawelke |author3=D. Mootz |author4=E. H. Appelman | title = The Crystal Structure of Hypofluorous Acid : Chain Formation by O-H · · · O Hydrogen Bonds | journal = ] | year = 1988 | volume = 27 | issue = 3 | pages = 392–3 | doi = 10.1002/anie.198803921}}</ref> |
|
|
:{{chem2|2 HOF → 2 HF + O2}} |
|
|
This reaction is catalyzed by water.<ref name=Secondary /> |
|
|
|
|
|
|
It was isolated in the pure form by passing {{chem2|F2}} gas over ice at −40 °C, rapidly collecting the HOF gas away from the ice, and condensing it:<ref name=Secondary>{{Cite journal |last=Appelman |first=Evan H. |date=1973-04-01 |title=Nonexistent compounds. Two case histories |url=https://pubs.acs.org/doi/abs/10.1021/ar50064a001 |journal=Accounts of Chemical Research |language=en |volume=6 |issue=4 |pages=113–117 |doi=10.1021/ar50064a001 |issn=0001-4842}}</ref> |
|
'''Hypofluorous acid''' is the ] with the formula HOF. It is an intermediate in the ] of ] by ], which produces ] and ]. 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 · · · O Hydrogen Bonds | journal = ] | 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. |
|
|
|
:{{chem2|F2 + H2O → HOF + HF}} |
|
|
|
|
|
The compound has been characterized in the solid phase by ]<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. |
|
The compound has been characterized in the solid phase by ]<ref name="Poll"/> as a ] with an angle of 101°. The O–F and O–H bond lengths are 144.2 and 96.4 ]s, 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°). |
|
|
|
|
|
|
] chemists commonly call a solution of hypofluorous acid in ] (generated ''in situ'' by passing gaseous ] through water in acetonitrile) Rozen's reagent.<ref name=Rozen>For Rozen's original popularizations, see: |
|
For fluorine, the only known ] is hypofluorous acid, HOF, in which fluorine is in the -1 oxidation state. It can be made by passing F<sub>2</sub> |
|
|
|
* {{cite journal|last=Rozen|first=Shlomo|title=Hypofluorous Acid|date=2001|doi=10.1002/047084289X.rh074|journal=Encyclopedia of Reagents for Organic Synthesis|isbn=0471936235}} |
|
gas over ice at -40 °C and collecting the HOF gas which |
|
|
|
* {{cite journal|doi=10.1021/ar500107b|pmid=24871453|title=HOF·CH<sub>3</sub>CN: Probably the Best Oxygen Transfer Agent Organic Chemistry Has To Offer|last=Rozen|first=Shlomo|year=2014|journal=Acc. Chem. Res.|volume=47|issue=8|pages=2378–2389}} |
|
condenses. It decomposes at room temperature to form HF and O |
|
|
|
|
|
|
|
For subsequent use, see, e.g. |
|
F<sub>2</sub> + H<sub>2</sub>O → HOF + HF |
|
|
|
* {{Cite journal|last1=Singh|first1=Raman|last2=Kaur|first2=Rajneesh|last3=Gupta|first3=Tarang|last4=Kulbir|first4=Kulbir|last5=Singh|first5=Kuldeep|date=2019|title=Applications of Rozen's Reagent in Oxygen-Transfer and C-H Activation Reactions|doi=10.1055/s-0037-1609638|journal=Synthesis|volume=51|issue=2|pages=371–383|s2cid=104572566}} |
|
|
* {{cite journal|last1=Dell|first1=Emma J.|last2=Campos|first2=Luis M.|title=The preparation of thiophene-''S'',''S''-dioxides and their role in organic electronics|doi=10.1039/C2JM31220D|journal=J. Mater. Chem.|year=2012|volume=22|issue=26|pages=12945–12952}} |
|
|
</ref> |
|
|
|
|
|
|
== Difference from other hypohalous acids == |
|
Hypofluorous acid in acetonitrile (generated ''in situ'' by passing gaseous fluorine through "wet" ]) serves as a highly ] oxygen-transfer agent.<ref>{{cite journal | author = S. Rozen, M. Brand | journal = ] | 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 = ] | 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 ] with this reagent yielded the previously elusive ''1,10-phenanthroline dioxide'',<ref>{{cite journal | author = S. Rozen, S. Dayan | journal = ] | 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 = ] | title = Phenanthroline Di-N-oxides | year = 1946 | volume = 68 | issue = 3 | pages = 403 | doi = 10.1021/ja01207a019}}</ref> |
|
|
|
The formal ] of ] in hypofluorous acid and hypofluorite is 0; the same oxidation state found in ]. In most oxygen compounds, including the other hypohalous acids, oxygen takes on a state of -2. The oxygen (0) atom is the root of hypofluorous acid's strength as an oxidizer, in contrast to the halogen (+1) atom in other hypohalic acids. |
|
|
|
|
|
This alters the acid's chemistry. Where reduction of a general hypohalous acid reduces the halogen atom and yields the corresponding elemental halogen gas, |
|
|
:{{chem2|2 HOX + 2 H+ + 2 e- -> 2 H2O + X2}} |
|
|
reduction of hypofluorous acid instead reduces the oxygen atom and yields ] directly. |
|
|
:{{chem2|HOF + H+ + 2 e- -> H2O + F-}} |
|
|
Unlike other hypohalous acids, HOF is a weaker oxidant than elemental fluorine. |
|
|
|
|
|
==Hypofluorites== |
|
|
Hypofluorites are formally derivatives of {{chem2|OF−}}, which is the ] of hypofluorous acid. One example is ] ({{chem2|CF3OF}}), which is a ] ] of hypofluorous acid. The conjugate base is known in salts such as ]. |
|
|
|
|
|
==See also== |
|
==See also== |
| Line 56: |
Line 89: |
|
{{Hydrogen compounds}} |
|
{{Hydrogen compounds}} |
|
|
|
|
|
] |
|
] |
|
|
] |
|
] |
|
] |
|
] |
|
] |
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|