Fluorosulfonate

Fluorosulfonate, in organic chemistry, is a functional group that has the chemical formula F-SO2-R, and typically is a very good leaving group. 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. They form a series of salts with metal and organic cations called fluorosulfates.

Fluorosulfonate

Fluorosulfate ion
Identifiers
3D model (JSmol)
ChemSpider
  • (ion): InChI=1S/FHO3S/c1-5(2,3)4/h(H,2,3,4)/p-1
    Key: UQSQSQZYBQSBJZ-UHFFFAOYSA-M
  • (ion): [O-]S(=O)(=O)F
Properties
FO3S−
Molar mass 99.06 g·mol−1
Related compounds
Other anions
 Chlorosulfate
Related compounds
 Fluorine fluorosulfonate, Sulfuryl fluoride, Trifluorosulfate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Organic (alkyl) fluorosulfonates are usually strong alkylation agents, similar to triflate esters (F3C-SO2-OR).[1] 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.

General chemical structure of a fluorosulfate ester. In Fluorosulfonates, sulfur atom is directly bonded to a non-oxygen atom such as carbon.

See also

References
  1. Revathi, Lekkala; Ravindar, Lekkala; Leng, Jing; Rakesh, Kadalipura Puttaswamy; Qin, Hua-Li (2018). "Synthesis and Chemical Transformations of Fluorosulfates". Asian Journal of Organic Chemistry. 7 (4): 662–682. doi:10.1002/ajoc.201700591.


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