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fluorosulfonate

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EntityQ1002155· pop 8· linked from 12 articles

fluorosulfonate

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Also known as fluorosulfate, sulfurofluoridate

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.

Chemical data

Formula
FO3S-
Molecular weight
99.06 g/mol
SMILES
[O-]S(=O)(=O)F
InChIKey
UQSQSQZYBQSBJZ-UHFFFAOYSA-M
XLogP
-0.4
Polar surface area
65.6 Ų
H-bond donors
0
H-bond acceptors
4
Formal charge
-1

via PubChem

Wikidata facts

Mass
98.955218
Show 3 more facts
canonical SMILES
[O-]S(=O)(=O)F
conjugate acid
fluorosulfonic acid
chemical formula
FO₃S⁻
Sources (2)

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Encyclopedic overview

2 sections
Contents
  • See also
  • References

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

Excerpted from Wikipedia’s “fluorosulfonate” article, available under the CC BY-SA 4.0 licence.

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