Sulfur trioxide pyridine complex

Chemical compound From Wikipedia, the free encyclopedia

Sulfur trioxide pyridine complex is the compound with the formula C5H5NSO3. It is a colourless solid that dissolves in polar organic solvents. It is the adduct formed from the Lewis base pyridine and the Lewis acid sulfur trioxide. The compound is mainly used as a source of sulfur trioxide, for example in the synthesis of sulfate esters from alcohols:[1]

ROH + C5H5NSO3 → [C5H5NH]+[ROSO3]
Quick Facts Identifiers, Properties ...
Sulfur trioxide pyridine complex
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Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.043.334
  • InChI=1S/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H; Y
    Key: UDYFLDICVHJSOY-UHFFFAOYSA-N Y
  • InChI=1/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H;
    Key: UDYFLDICVHJSOY-UHFFFAOYAG
  • O=S(=O)=O.n1ccccc1
Properties
C5H5NSO3
Molar mass 159.16 g/mol
Appearance white solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It also is useful for sulfamations:

R2NH + C5H5NSO3 → C5H5N + R2NSO3H

The compound is used for sulfonylation reactions, especially in the sulfonylation of furans.[2] It is also an activating electrophile in a Parikh-Doering oxidation.[3]

References

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