text:
Pyridinium
From Wikipedia, the free encyclopedia
Jump to: navigation, search
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. (December 2009) (Learn how and when to remove this template message)
Pyridinium
Names
IUPAC name
pyridinium
Identifiers
CAS Number
16969-45-2 N
3D model (JSmol)
Interactive image
ChemSpider
4169387 Y
PubChem CID
4989215
InChI[show]
InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1 Y
Key: JUJWROOIHBZHMG-UHFFFAOYSA-O Y
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+1
Key: JUJWROOIHBZHMG-UHFFFAOYSA-O
SMILES[show]
c1cc[nH+]cc1
Properties
Chemical formula
C
5H
6N+
Molar mass 80.11 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is Y N ?)
Infobox references
Pyridinium is the cationic conjugate acid 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 electrophilic acylium ion, rendering it even more reactive. Because the protonation involves only the lone pair electrons of nitrogen in pyridine, pyridinium is an aromatic ion, as determined through Hückel's rule.[1] It is isoelectronic to benzene.
See also[edit]
Pyridinium chlorochromate
Jump up ^ http://crab.rutgers.edu/~alroche/Ch16.pdf

This article about an organic compound is a stub. You can help Wikipedia by expanding it.
v
t
e
Retrieved from "https://en.wikipedia.org/w/index.php?title=Pyridinium&oldid=792742428"
Categories:
Pyridinium compounds
Organic compound stubs
Hidden categories:
Articles lacking sources from December 2009
All articles lacking sources
Chemical articles with multiple compound IDs
Multiple chemicals in an infobox that need indexing
Articles without EBI source
Articles without KEGG source
Articles without UNII source
Articles with changed CASNo identifier
Articles containing unverified chemical infoboxes
All stub articles
Navigation menu
Personal tools
Not logged in
Talk
Contributions
Create account
Log in
Namespaces
Article
Talk
Variants
Views
Read
Edit
View history
More
Search
Navigation
Main page
Contents
Featured content
Current events
Random article
Donate to Wikipedia
Wikipedia store
Interaction
Help
About Wikipedia
Community portal
Recent changes
Contact page
Tools
What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Wikidata item
Cite this page
Print/export
Create a book
Download as PDF
Printable version
Languages
Español
فارسی
Français
Nederlands
Српски / srpski
Srpskohrvatski / српскохрватски
Edit links
This page was last edited on 28 July 2017, at 11:15.
Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.
Privacy policy
About Wikipedia
Disclaimers
Contact Wikipedia
Developers
Cookie statement
Mobile view

key: html

type: local

value: div

attrs: id class

values: mw-page-base noprint

values: mw-head-base noprint

attrs: id class style

value: a

attrs: id class lang

values: firstHeading firstHeading en

values: siteSub noprint

values: jump-to-nav mw-jump

value: img

attrs: alt src width height srcset data-file-width data-file-height

attrs: href class

value: td

attrs: href title

value: b

attrs: class href

values: Help:Introduction to referencing with Wiki Markup/1

value: span

value: i

value: small

values: plainlinks metadata ambox ambox-content ambox-Unreferenced

values: background: #f8eaba; text-align: center;

values: chemapps.stolaf.edu (3D interactive model)

values: font-size: 105%; text-align:left; font-weight:normal; background:transparent;

values: border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left; word-wrap:break-word; text-indent:-1.5em; font-size:11px; line-height:120%;

values: list-style: none none; margin-left: 0px; word-break: break-all; font-size: 105%; margin-top: 0px; margin-bottom: 0px; line-height: inherit; display: none;

values:
NavFrame collapsed
border: none; padding: 0;
NavFrame1

values: Simplified molecular-input line-entry system

values: border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:11px; line-height:120%;

values:
NavFrame collapsed
border: none; padding: 0;
NavFrame2

values: margin:0 auto; text-align:left; padding:0.1em 0;line-height:1.2em;

values: background:#f8eaba; border-top:2px solid transparent;

values: width:40%; max-height:1px; border-top:2px solid transparent; border-right:1px solid transparent;

values: width:60%; max-height:1px; border-top:2px solid transparent; border-left:1px solid transparent;

values:
/wiki/Friedel-Crafts_acylation
mw-redirect
Friedel-Crafts acylation

values:
reflist mw-references-wrap
list-style-type: decimal;

values: position: absolute; right: 15px; display: none;

values:
metadata plainlinks stub
presentation
background:transparent

values: Category:Articles lacking sources from December 2009

values: Category:Chemical articles with multiple compound IDs

values: Category:Multiple chemicals in an infobox that need indexing

values: Category:Articles with changed CASNo identifier

values: Category:Articles containing unverified chemical infoboxes

values: Discussion about edits from this IP address [ctrl-alt-n]

values: A list of edits made from this IP address [ctrl-alt-y]

values: You are encouraged to create an account and log in; however, it is not mandatory

values: You're encouraged to log in; however, it's not mandatory. [ctrl-alt-o]

values:
/wiki/Pyridinium
View the content page [ctrl-alt-c]
c

values: Discussion about the content page [ctrl-alt-t]

values: p-namespaces navigation vectorTabs p-namespaces-label

values:
p-variants
navigation
vectorMenu emptyPortlet
p-variants-label

values: Past revisions of this page [ctrl-alt-h]

values: p-views navigation vectorTabs p-views-label

values:
p-cactions
navigation
vectorMenu emptyPortlet
p-cactions-label

values:
mw-wiki-logo
/wiki/Main_Page
Visit the main page

values:
/wiki/Main_Page
Visit the main page [ctrl-alt-z]
z

values: Featured content – the best of Wikipedia

values: Find background information on current events

values:
/wiki/Special:Random
Load a random article [ctrl-alt-x]
x

values: portal navigation p-navigation p-navigation-label

values: Guidance on how to use and edit Wikipedia

values: About the project, what you can do, where to find things

values: A list of recent changes in the wiki [ctrl-alt-r]

values: portal navigation p-interaction p-interaction-label

values: List of all English Wikipedia pages containing links to this page [ctrl-alt-j]

values: Recent changes in pages linked from this page [ctrl-alt-k]

values:
/wiki/Wikipedia:File_Upload_Wizard
Upload files [ctrl-alt-u]
u

values: A list of all special pages [ctrl-alt-q]

values: Permanent link to this revision of the page

values: Link to connected data repository item [ctrl-alt-g]

values: Printable version of this page [ctrl-alt-p]

values:
uls-settings-trigger
Language settings
0
button
true

values:
https://es.wikipedia.org/wiki/Piridinio
Piridinio – Spanish
es
es
interlanguage-link-target

values: پیریدینیوم – Persian

values: /static/images/wikimedia-button-1.5x.png 1.5x, /static/images/wikimedia-button-2x.png 2x

values: /static/images/poweredby_mediawiki_132x47.png 1.5x, /static/images/poweredby_mediawiki_176x62.png 2x

values:
suggestions
display: none; font-size: 13px;

values: mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-Pyridinium rootpage-Pyridinium vector-nav-directionality skin-vector action-view