Fluorosulfonate, in organic
chemistry
Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...
, is a
functional group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
that has the chemical formula F-SO
2-R, and typically is a very good
leaving group
In organic chemistry, a leaving group typically means a Chemical species, molecular fragment that departs with an electron, electron pair during a reaction step with heterolysis (chemistry), heterolytic bond cleavage. In this usage, a ''leaving gr ...
. 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-SO
2-O
−, the conjugate base of
fluorosulfonic acid
Fluorosulfuric acid (IUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula . It is one of the strongest acids commercially available. It is a tetrahedral molecule and is closely related to sulfuric acid, , substitu ...
. They form a series of salts with metal and organic cations called
fluorosulfates.
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 group is derived from a cy ...
) fluorosulfonates are usually strong
alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. 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 effecting al ...
agents, similar to
triflate
In organic chemistry, triflate (Preferred IUPAC name, systematic name: trifluoromethanesulfonate), is a functional group with the Chemical formula, formula and Chemical structure, structure . The triflate group is often represented by , as opp ...
esters (F
3C-SO
2-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.
:
See also
*
Fluorosulfite
*
Methyl fluorosulfonate
Methyl fluorosulfonate, also known as magic methyl, is the organic compound with the formula FSO2OCH3. It is a colorless liquid that is used as a strong methylating agent in organic synthesis. Because of its extreme toxicity, it has largely been ...
References
Functional groups
Leaving groups
Sulfonates
{{organic-chemistry-stub