| Revision as of 12:04, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444076095 of page Pyridinium for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 13:48, 28 September 2023 edit Trappist the monk (talk | contribs)Administrators479,889 editsm cite repair;Tag: AWB |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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| verifiedrevid = 444074249 |
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| ImageFileL1 = Pyridinium.svg |
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|verifiedrevid = 464376936 |
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| ImageFileR1 = Pyridinium-3D-balls.png |
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|ImageFileL1 = Pyridinium.svg |
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|ImageFileR1 = Pyridinium-3D-balls.png |
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| IUPACName = pyridinium |
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|ImageSizeR1 = 120px |
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| OtherNames = |
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|PIN = Pyridin-1-ium |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChI = 1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1 |
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|InChI = 1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1 |
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| InChIKey1 = JUJWROOIHBZHMG-UHFFFAOYSA-O |
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|InChIKey1 = JUJWROOIHBZHMG-UHFFFAOYSA-O |
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| InChI1 = 1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1 |
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|InChI1 = 1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1 |
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| CASNo = <!-- blanked - oldvalue: 16969-45-2 --> |
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|CASNo = 16969-45-2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 4989215 |
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|CASNo_Ref = {{cascite|correct|PubChem}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII =RNZ2DM8Q8K |
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| ChemSpiderID = 4169387 |
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|PubChem = 4989215 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = JUJWROOIHBZHMG-UHFFFAOYSA-O |
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|ChemSpiderID = 4169387 |
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| SMILES = 1ccccc1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = JUJWROOIHBZHMG-UHFFFAOYSA-O |
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| StdInChI =1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1 |
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|SMILES = c1cccc1 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Section2 = {{Chembox Properties |
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|StdInChI = 1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1 |
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| C=5|H=6|N=1 |
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| Section3 = {{Chembox Hazards |
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|Formula = {{chem2|+}} |
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|C=5 | H=6 | N=1 |
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|ConjugateBase = ] |
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|pKa = ~5 <ref>{{cite journal|last1=Linnell|first1=Robert|title=Notes – Dissociation Constants of 2-Substituted Pyridines|journal=Journal of Organic Chemistry|volume=25|page=290|year=1960|doi=10.1021/jo01072a623|issue=2}}</ref><ref>{{cite journal|last1=Pearson|first1=Ralph G.|title=Rates of Ionization of Pseudo Acids.1V. Steric Effects in the Base-catalyzed Ionization of Nitroethane|last2=Williams|first2=Forrest V.|journal=Journal of the American Chemical Society|volume=75|page=3073|year=1953|doi=10.1021/ja01109a008|issue=13}}</ref> |
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'''Pyridinium''' refers to the ] {{chem2|+}}. It is the ] of ]. Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines. They are prepared by treating pyridine with acids.<ref>{{cite journal|title=Fluorinations With Pyridinium Polyhydrogen Fluoride Reagent: 1-Fluoroadamantane|author=George A. Olah |author2=Michael Watkins |journal=Org. Synth.|year=1978|volume=58|page=75|doi=10.15227/orgsyn.058.0075}}</ref> |
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As pyridine is often used as an ] in ]s, pyridinium salts are produced in many ]. Its ] are often ] in the organic solvent, so ] of the pyridinium leaving group complex is an indication of the progress of the reaction. |
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Pyridinium cations are ], as determined through ].<ref>{{Cite web | url = http://crab.rutgers.edu/~alroche/Ch16.pdf | title = Aromatic Compounds | publisher = Alex Roche, Rutgers University}}</ref> They are ] with ]. |
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==''N''-Alkylpyridinium cations== |
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] is a ''N''-alkylpyridinium cation that occurs widely in life.]] |
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When the acidic proton is replaced by ], the compounds are called ''N''-alkylpyridinium. A simple representative is ] ({{chem2|+}}). These pyridinium intermediates have been used as electrophiles in synthetic organic chemistry to build dearomatized congeners called dihydropyridines, as demonstrated in one example from Smith in 2021.<ref>{{Cite journal|last1=Grigolo|first1=Thiago A.|last2=Subhit|first2=Ariana R.|last3=Smith|first3=Joel M.|date=2021-09-03|title=Regioselective Asymmetric Alkynylation of N-Alkyl Pyridiniums|journal=Organic Letters|volume=23|issue=17|pages=6703–6708|doi=10.1021/acs.orglett.1c02276|pmid=34474575 |s2cid=237401193 |issn=1523-7060}}</ref> Earlier, the same research group also delineated the rules surrounding regioselectivities associated with adding nucleophiles to pyridinium electrophiles with varying substituents.<ref>{{Cite journal|last1=Knight|first1=Brian J.|last2=Tolchin|first2=Zachary A.|last3=Smith|first3=Joel M.|date=2021-03-11|title=A predictive model for additions to N-alkyl pyridiniums|url=https://pubs.rsc.org/en/content/articlelanding/2021/cc/d1cc00056j|journal=Chemical Communications|language=en|volume=57|issue=21|pages=2693–2696|doi=10.1039/D1CC00056J|pmid=33595047 |s2cid=231945207 |issn=1364-548X}}</ref> From a commercial perspective, an important pyridinium compound is the ] ].<ref name=Ullmann>{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}</ref> |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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] |