Fluorosulfonate, in organic chemistry, is a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...

that has the chemical formula F-SO₂-R, and typically is a very good

leaving group In chemistry, a leaving group is defined by the IUPAC as an atom or group of atoms that detaches from the main or residual part of a substrate during a reaction or elementary step of a reaction. However, in common usage, the term is often limited ...

. In organic chemistry, fluorosulfonate is different than fluorosulfate. In fluorosulfonates, sulfur atom is directly bonded to a non-oxygen atom such as carbon. In inorganic chemistry, fluorosulfonate is another term for fluorosulfate, the anion F-SO₂-O⁻, the conjugate base of

fluorosulfonic acid Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula HSO3F. It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, H2SO ...

. They form a series of salts with metal and organic cations called

fluorosulfates The fluorosulfates or fluorosulfonates are a set of salts of fluorosulfuric acid with an ion formula SO3F−. The fluorosulfate anion can be treated as though it were a hydrogen sulfate anion with hydroxyl substituted by fluorine. The fluorosulfate ...

. Organic (

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloal ...

) fluorosulfonates are usually strong

alkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effectin ...

agents, similar to

triflate In organic chemistry, triflate ( systematic name: trifluoromethanesulfonate), is a functional group with the formula and structure . The triflate group is often represented by , as opposed to −Tf, which is the triflyl group, . For example, ...

esters (F₃C-SO₂-OR). But unlike the triflate group, the fluorosulfonate group is not stable against hydrolysis. Therefore, fluorosulfonate esters are less frequently used as alkylation agents than triflate esters.

References

Functional groups Leaving groups Sulfonates {{chemistry-stub

See also

References