Pyridinium - Misplaced Pages

This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 15:24, 10 August 2011 (Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox validati). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 15:24, 10 August 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox validati)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)

This article does not cite any sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed.
Find sources: "Pyridinium" – news · newspapers · books · scholar · JSTOR (December 2009) (Learn how and when to remove this message)

Pyridinium

Names

IUPAC name pyridinium

Identifiers

CAS Number

16969-45-2

3D model (JSmol)

Interactive image

ChemSpider

4169387

PubChem CID

4989215

CompTox Dashboard (EPA)

DTXSID20407294

InChI

InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1Key: JUJWROOIHBZHMG-UHFFFAOYSA-O
InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1
InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1Key: JUJWROOIHBZHMG-UHFFFAOYSA-O

SMILES

1ccccc1

Properties

Chemical formula

C₅H₆N

Molar mass

80.110 g·mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

Y verify (what is ?) Infobox references

Chemical compound

Pyridinium refers to the cationic form of pyridine. This can either be due to protonation of the ring nitrogen or because of addition of a substituent to the ring nitrogen, typically via alkylation. The lone pair of electrons on the nitrogen atom of pyridine is not delocalized, and thus pyridine can be protonated easily. Pyridine is often used as an organic base in chemical reactions, thus the pyridinium ion is produced as the counter ion to the leaving group in the reaction. This complex is often insoluble in the organic solvent, so precipitation of the pyridinium leaving group complex is an indication of the progress of the reaction. The pyridinium ion also plays a role in Friedel-Crafts acylation. When pyridine is included, it forms a complex with the electrophillic acylium ion, rendering it even more reactive.

See also