Hypofluorous acid
Gas-phase structure
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Names | |
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IUPAC name
Hypofluorous acid
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Other names
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
HOF | |
Molar mass | 36.0057 g/mol |
Appearance | pale yellow liquid above −117 °C white solid below −117 °C |
Melting point | −117 °C (−179 °F; 156 K) |
Boiling point | decomposes at 0 °C (32 °F; 273 K)[citation needed] |
Structure | |
Cs | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Explosive, strong oxidizer, corrosive |
NFPA 704 (fire diamond) | |
Related compounds | |
Other cations
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Lithium hypofluorite |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hypofluorous acid,
- 2 HOF → 2 HF + O2
This reaction is catalyzed by water.[2]
It was isolated in the pure form by passing F2 gas over ice at −40 °C, rapidly collecting the HOF gas away from the ice, and condensing it:[2]
- F2 + H2O → HOF + HF
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°).
Thiophene chemists commonly call a solution of hypofluorous acid in acetonitrile (generated in situ by passing gaseous fluorine through water in acetonitrile) Rozen's reagent.[3]
Hypofluorites
Hypofluorites are formally derivatives of OF−, which is the
See also
- Hypochlorous acid, a related compound that is more technologically important but has not been obtained in pure form.
References
- ^ .
- ^ ISSN 0001-4842.
- ^ For Rozen's original popularizations, see:
- Rozen, Shlomo (2001). "Hypofluorous Acid". Encyclopedia of Reagents for Organic Synthesis. ISBN 0471936235.
- Rozen, Shlomo (2014). "HOF·CH3CN: Probably the Best Oxygen Transfer Agent Organic Chemistry Has To Offer". Acc. Chem. Res. 47 (8): 2378–2389. PMID 24871453.
- Singh, Raman; Kaur, Rajneesh; Gupta, Tarang; Kulbir, Kulbir; Singh, Kuldeep (2019). "Applications of Rozen's Reagent in Oxygen-Transfer and C-H Activation Reactions". Synthesis. 51 (2): 371–383. S2CID 104572566.
- Dell, Emma J.; Campos, Luis M. (2012). "The preparation of thiophene-S,S-dioxides and their role in organic electronics". J. Mater. Chem. 22 (26): 12945–12952. .
- Rozen, Shlomo (2001). "Hypofluorous Acid". Encyclopedia of Reagents for Organic Synthesis.