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Pyridinium information


Pyridinium
Names
Preferred IUPAC name
Pyridin-1-ium
Identifiers
CAS Number
  • 16969-45-2 checkY[PubChem]
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4169387 checkY
PubChem CID
  • 4989215
UNII
  • RNZ2DM8Q8K checkY
CompTox Dashboard (EPA)
  • DTXSID20407294 Edit this at Wikidata
InChI
  • InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H/p+1 checkY
    Key: JUJWROOIHBZHMG-UHFFFAOYSA-O checkY
  • 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
  • c1cc[nH+]cc1
Properties
Chemical formula
[C5H5NH]+
Molar mass 80.110 g·mol−1
Acidity (pKa) ~5 [1][2]
Conjugate base Pyridine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pyridinium refers to the cation [C5H5NH]+. It is the conjugate acid of pyridine. Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines. They are prepared by treating pyridine with acids.[3]

As pyridine is often used as an organic base in chemical reactions, pyridinium salts are produced in many acid-base reactions. Its salts are often insoluble in the organic solvent, so precipitation of the pyridinium leaving group complex is an indication of the progress of the reaction.

Pyridinium cations are aromatic, as determined through Hückel's rule.[4] They are isoelectronic with benzene.

  1. ^ Linnell, Robert (1960). "Notes – Dissociation Constants of 2-Substituted Pyridines". Journal of Organic Chemistry. 25 (2): 290. doi:10.1021/jo01072a623.
  2. ^ Pearson, Ralph G.; Williams, Forrest V. (1953). "Rates of Ionization of Pseudo Acids.1V. Steric Effects in the Base-catalyzed Ionization of Nitroethane". Journal of the American Chemical Society. 75 (13): 3073. doi:10.1021/ja01109a008.
  3. ^ George A. Olah; Michael Watkins (1978). "Fluorinations With Pyridinium Polyhydrogen Fluoride Reagent: 1-Fluoroadamantane". Org. Synth. 58: 75. doi:10.15227/orgsyn.058.0075.
  4. ^ "Aromatic Compounds" (PDF). Alex Roche, Rutgers University.

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Pyridinium

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Pyridinium refers to the cation [C5H5NH]+. It is the conjugate acid of pyridine. Many related cations are known involving substituted pyridines, e.g. picolines...

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Pyridinium chloride

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Pyridinium chloride is an organic chemical compound with a formula of C5H5NHCl. Pyridinium chloride can be produced by passing hydrogen chloride in pyridine...

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Pyridinium perbromide

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Pyridinium perbromide (also called pyridinium bromide perbromide, pyridine hydrobromide perbromide, or pyridinium tribromide) is an organic chemical composed...

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Pyridine

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Protonation gives pyridinium, C5H5NH+.The pKa of the conjugate acid (the pyridinium cation) is 5.25. The structures of pyridine and pyridinium are almost identical...

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Cornforth reagent

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The pyridinium dichromate (PDC) or Cornforth reagent is a pyridinium salt of dichromate with the chemical formula [C5H5NH]2[Cr2O7]. This compound is named...

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Pyridinium chlorochromate

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Pyridinium chlorochromate (PCC) is a yellow-orange salt with the formula [C5H5NH]+[CrO3Cl]−. It is a reagent in organic synthesis used primarily for oxidation...

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Cetylpyridinium chloride

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cetyl alcohol that was first isolated from the whale oil (Latin: cetus); pyridinium refers to the cation [C5H5NH]+, the conjugate acid of pyridine; chloride...

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Photopolymer

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cationic initiators, including onium salts, organometallic compounds and pyridinium salts. As mentioned earlier, one of the drawbacks of the photoinitiators...

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Zincke reaction

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named after Theodor Zincke, in which a pyridine is transformed into a pyridinium salt by reaction with 2,4-dinitro-chlorobenzene and a primary amine. The...

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Adipaldehyde

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commercialization. It has been prepared by oxidation of 1,6-hexanediol with pyridinium chlorochromate. Hardy, P. M.; Nicholls, A. C.; Rydon, H. N. (1972). "The...

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Alcohol oxidation

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salts, featuring the pyridinium cation (C5H5NH+). pyridinium dichromate (PDC) is the pyridium salt of dichromate, [Cr2O7]2-. pyridinium chlorochromate (PCC)...

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Polypyridinium salts

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Polypyridinium salts are members of a class of main chain polyelectrolytes. DeRosa, Thomas F. (2009-12-15). Patent Applications: A Tool for Identifying...

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Cephaloridine

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Its chemical structure contains 3 cephems, 4 carboxyl groups and three pyridinium methyl groups. Cephaloridine is mainly used in veterinary practice. It...

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Oxidizing agent

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compounds such as chromic and dichromic acids and chromium trioxide, pyridinium chlorochromate (PCC), and chromate/dichromate compounds such as Sodium...

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Pralidoxime

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Stojiljković MP (December 2006). "Current understanding of the application of pyridinium oximes as cholinesterase reactivators in treatment of organophosphate...

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Transamination

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enzymatic Lys residue. The Schiff base, which is conjugated to the enzyme's pyridinium ring, is the focus of the coenzyme activity. The product of transamination...

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Ionic liquid

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1970s and 1980s, ionic liquids based on alkyl-substituted imidazolium and pyridinium cations, with halide or tetrahalogenoaluminate anions, were developed...

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List of organic salts

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Mellite Tetrapropylammonium perruthenate Collidinium p-toluenesulfonate Pyridinium chloride Tetrasodium EDTA Lithium diisopropylamide Lithium bis(trimethylsilyl)amide...

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Collins reagent

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alternative to the Jones reagent and pyridinium chlorochromate (PCC) when oxidizing secondary alcohols to ketones. PCC and pyridinium dichromate (PDC) oxidations...

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Basic aromatic ring

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Basic aromatic compounds get protonated and form aromatic cations (e.g. pyridinium) under acidic conditions. Typical examples of basic aromatic rings are...

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Tetrahydrocannabinol

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ChATTooltip Choline acetyltransferase Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine...

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Iodine value

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For educational purposes, Simurdiak et al. (2016) suggested the use of pyridinium tribromide as bromination reagent which is more safer in chemistry class...

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PPTS

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propulsion Prospective Piloted Transport System, a Russian spacecraft Pyridinium p-toluenesulfonate, a chemical reagent Point perfect transcription services...

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Ketone

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formation of an acetal, for example. Acids as weak as pyridinium cation (as found in pyridinium tosylate) with a pKa of 5.2 are able to serve as catalysts...

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