| Revision as of 13:22, 15 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox validation← Previous edit |
Latest revision as of 23:44, 21 July 2023 edit undoFadesga (talk | contribs)Autopatrolled, Extended confirmed users263,401 edits →References |
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{{chembox |
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{{chembox |
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| verifiedrevid = 450636649 |
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| verifiedrevid = 450637936 |
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| ImageFileL1 = Sulfur-trioxide-pyridine-complex-2D-skeletal.png |
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| ImageFileL1 = Sulfur-trioxide-pyridine-complex-2D-skeletal.png |
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| ImageSizeL1 = |
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| IUPACName = |
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| IUPACName = |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| PubChem = |
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| CASNo = 26412-87-3 |
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| CASNo = 26412-87-3 |
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| PubChem = 168533 |
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| PubChem = 168533 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 147422 |
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| ChemSpiderID = 147422 |
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| SMILES = O=S(=O)=O.n1ccccc1 |
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| SMILES = O=S(=O)=O.n1ccccc1 |
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| InChI = 1/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H; |
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| InChI = 1/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H; |
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| InChIKey = UDYFLDICVHJSOY-UHFFFAOYAG |
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| InChIKey = UDYFLDICVHJSOY-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H; |
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| StdInChI = 1S/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H; |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UDYFLDICVHJSOY-UHFFFAOYSA-N |
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| StdInChIKey = UDYFLDICVHJSOY-UHFFFAOYSA-N |
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}} |
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| SMILES = }} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub> |
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| Formula = C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub> |
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| MolarMass = 159.16 g/mol |
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| MolarMass = 159.16 g/mol |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt = |
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| Autoignition = }} |
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}} |
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}}<!-- Text starts below--> |
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}}<!-- Text starts below--> |
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'''Sulfur trioxide pyridine complex''' is a ] formed where the ] on the ] of the ] binds to the ] of the ]. The resulting compound is used as an activating ] in a ].<ref>{{cite journal | title = Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide | author = Jekishan R. Parikh, William v. E. Doering |journal = ] | year = 1967 | volume = 89 | pages = 5505–5507 | doi = 10.1021/ja00997a067}}</ref> |
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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 ] formed from the ] ] and the ] ]. The compound is mainly used as a source of sulfur trioxide, for example in the synthesis of ]s from ]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> |
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:ROH + C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub> → <sup>+</sup><sup>−</sup> |
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It also is useful for ]s: |
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: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 |
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The compound is used for sulfonylation reactions, especially in the sulfonylation of ]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 ] in a ].<ref>{{cite journal | title = Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide | author = Jekishan R. Parikh, William v. E. Doering |journal = ] | year = 1967 | volume = 89 | pages = 5505–5507 | doi = 10.1021/ja00997a067 | issue = 21}}</ref> |
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The compound strongly violates the ], as sulfur here has 12 or 14 electrons in its valence shells, depending on whether the S-N bond is viewed as ] or not. |
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==References== |
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==References== |
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