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Fluorosulfonate

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Fluorosulfonate

Fluorosulfate ion
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • (ion): InChI=1S/FHO3S/c1-5(2,3)4/h(H,2,3,4)/p-1Key: UQSQSQZYBQSBJZ-UHFFFAOYSA-M
SMILES
  • (ion): S(=O)(=O)F
Properties
Chemical formula FO3S
Molar mass 99.06 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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.

Organic (alkyl) fluorosulfonates are usually strong alkylation agents, similar to triflate 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.

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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