View source for Sulfur trioxide pyridine complex

{{chembox
| Watchedfields = changed
| verifiedrevid = 450637936
| ImageFileL1 = Sulfur-trioxide-pyridine-complex-2D-skeletal.png
| ImageSizeL1 =
| ImageFileR1 = Sulfur-trioxide-pyridine-complex-3D-vdW.png
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| IUPACName = 
| OtherNames = 
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 26412-87-3
| PubChem = 168533
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 147422
| SMILES = O=S(=O)=O.n1ccccc1
| InChI = 1/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H;
| InChIKey = UDYFLDICVHJSOY-UHFFFAOYAG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H;
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UDYFLDICVHJSOY-UHFFFAOYSA-N
 }}
|Section2={{Chembox Properties
| Formula = C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub>
| MolarMass = 159.16 g/mol
| Appearance = white solid 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = }}
|Section3={{Chembox Hazards
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| FlashPt = 
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'''Sulfur trioxide pyridine complex''' is the compound with the formula C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub>.  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 ester]]s from [[Alcohol (chemistry)|alcohol]]s:<ref>Thomas T. Tidwell "Sulfur Trioxide–Pyridine" Encyclopedia of Reagents for Organic Synthesis 2001,  John Wiley & Sons.  {{doi|10.1002/047084289X.rs139m}}. Article Online Posting Date: April 15, 2001</ref>
:ROH  +  C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub>   →   [C<sub>5</sub>H<sub>5</sub>NH]<sup>+</sup>[ROSO<sub>3</sub>]<sup>−</sup>
It also is useful for [[sulfamation]]s:
:R<sub>2</sub>NH  +  C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub>   →   C<sub>5</sub>H<sub>5</sub>N   +  R<sub>2</sub>NSO<sub>3</sub>H

The compound is used for sulfonylation reactions, especially in the sulfonylation of [[furan]]s.<ref>{{Cite web|url=http://www.imperial.ac.uk/media/imperial-college/research-centres-and-groups/spivey-group/teaching/org2heteroaromatics/lecture451112.pdf|title=Heteroaromatic Chemistry Lectures 4 and 5|last=Spivey|first=Alan|date=12 March 2012|website=Imperial College Research|archive-url=|archive-date=|access-date=7 February 2017}}</ref> It is also an activating [[electrophile]] in a [[Parikh-Doering oxidation]].<ref>{{cite journal | title = Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide | author = Jekishan R. Parikh, William v. E. Doering |journal = [[J. Am. Chem. Soc.]] | year = 1967 | volume = 89 | pages = 5505–5507 | doi = 10.1021/ja00997a067 | issue = 21| bibcode = 1967JAChS..89.5505P }}</ref>

==References==
<references/>

[[Category:Sulfur(VI) compounds]]
[[Category:Pyridine complexes]]
[[Category:Reagents for organic chemistry]]


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