Hypofluorous acid

Hypofluorous acid is an unstable oxygen-containing acid of fluorine with the formula HOF, in which fluorine has oxidation state −1.

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O–F bond: A covalent bond between oxygen and fluorine, characterized by strong bond polarity and a relatively weak bond energy. This bond is the structural feature behind HOF’s short lifetime and reactivity.
Oxoacid: An acid containing hydrogen, oxygen, and another element, with acidic hydrogen commonly bonded to oxygen. HOF is an exceptionally simple oxoacid whose central element is fluorine.
Oxidizing agent: A substance that accepts electrons from another species and is reduced in a chemical reaction. HOF is used for its ability to oxidize organic compounds.
Georg Brauer: A German chemist known for work on inorganic chemistry and the preparation of inorganic compounds. Brauer’s handbook records early methods and chemistry associated with hypofluorous acid.
Perfluorinated oxidants: Oxidizing reagents containing multiple fluorine atoms, often used for oxygen-atom transfer. These reagents provide more stable alternatives for related oxidation reactions.
Oxidation state: A formal charge assignment used to track electron transfer in chemical compounds. It explains how fluorine can have oxidation state −1 in HOF despite its usual role as an oxidant.
Fluorine oxoacids: Oxygen-containing acids in which fluorine is the central element. This rare family provides the closest chemical classification for HOF.
Epoxidation: A reaction that converts an alkene into an epoxide by adding an oxygen atom across its double bond. HOF can transfer oxygen to alkenes, producing epoxides.
In situ preparation: Generation of a chemical species within the reaction mixture where it will be used. HOF is commonly generated in solution because it is difficult to isolate and store.
Hydrogen peroxide: A reactive compound with formula H₂O₂ used as an oxidant and disinfectant. It is a common oxygen-transfer oxidant that is substantially easier to handle than HOF.