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Pyrylium information


Pyrylium
Names
Preferred IUPAC name
Pyrylium[1]
Other names
Pyranium
Identifiers
CAS Number
  • 289-67-8 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1421881
ChEBI
  • CHEBI:36120 checkY
  • salt: CHEBI:59658
  • family: CHEBI:59657
ChemSpider
  • 7827742 checkY
Gmelin Reference
558560
PubChem CID
  • 9548819
CompTox Dashboard (EPA)
  • DTXSID40429539 Edit this at Wikidata
InChI
  • InChI=1S/C5H5O/c1-2-4-6-5-3-1/h1-5H/q+1 ☒N
    Key: WVIICGIFSIBFOG-UHFFFAOYSA-N ☒N
  • InChI=1/C5H5O/c1-2-4-6-5-3-1/h1-5H/q+1
    Key: WVIICGIFSIBFOG-UHFFFAOYAF
SMILES
  • [o+]1ccccc1
Properties
Chemical formula
C5H5O+
Molar mass 81.09 g/mol
Related compounds
Related compounds
thiopyrylium, selenopyrylium, telluropyrylium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Pyrylium is a cation (positive ion) with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1097. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

and 26 Related for: Pyrylium information

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Pyrylium

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Pyrylium is a cation (positive ion) with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively...

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Anthocyanidin

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and chromenylium (also called benzopyrylium) is a bicyclic version of pyrylium. The positive charge can move around the molecule. At least 31 monomeric...

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Phosphorine

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synthesized by Gottfried Märkl in 1966 by condensation of the corresponding pyrylium salt and phosphine or its equivalent ( P(CH2OH)3 and P(SiMe3)3). The (unsubstituted)...

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Pyran

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4H-pyran easily disproportionates to the corresponding dihydropyran and the pyrylium ion, which is easily hydrolyzed in aqueous medium. Although the pyrans...

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Selenopyrylium

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carbon atom, but actually selenium is substituted for the oxygen atom in pyrylium. In the Hantzsch-Widman system of nomenclature, it is called seleninium...

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Thiopyrylium

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analogous to the pyrylium cation with the oxygen atom replaced by a sulfur atom. Thiopyrylium salts are less reactive than the analogous pyrylium salts due to...

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Boratabenzene

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germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium Borazine Yuan, Yuanyuan;...

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Borabenzene

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stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium Borazine Boese, Roland;...

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Polyatomic ion

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Triphenylcarbenium (C6H5)3C+ Dihydrogen H+2 Phosphonium PH+4 Cyclopropenium C3H+3 Hydronium H3O+ Trifluoromethyl CF+3 Fluoronium H2F+ Pyrylium C5H5O+ Sulfonium H3S+...

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Benzene

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germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium Critics pointed out a problem...

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Aromaticity

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borabenzene, silabenzene, germanabenzene, stannabenzene, phosphorine or pyrylium salts the aromaticity is still retained. Aromaticity also occurs in compounds...

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Azulene

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the DPDB ligand Another synthesis route starts from the of pyridinium or pyrylium salts with cyclopentadienyl anion: Azulene can also be synthesized via...

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Heterocyclic compound

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not used) Pyridinium cation Oxygen Oxane Pyran (2H-Oxine is not used) Pyrylium cation Phosphorus Phosphinane Phosphinine Selenium Selenane Selenopyran...

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Arsabenzene

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6-triphenylphosphabenzene. This is achieved by treating 2,4,6-trisubstituted pyrylium salt with phosphanes. The first derivative of arsabenzene was 9-arsaanthracene...

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Telluropyrylium

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(This was measured in the crystal structure of tetraphenyl telluropyrylium-pyrylium monomethine fluoroborate. When the ring of telluropyrylium is fused with...

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Oxonium ion

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+1 cation derived by protonation of a hydride (includes oxonium ions) Pyrylium, a subtype of oxonium ion Sulfonium, a sulfur analog that can be chiral...

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Pyridine

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stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium 6-membered rings with two...

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Onium ion

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cations where oxygen is a member of a ring, RO+R (the ring may be aromatic) pyrylium, C5H5O+ tertiary sulfonium cations having one triple-bonded substitution...

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Germabenzene

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germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium Ebrahimi, A. A.; Ghiasi...

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Apigeninidin

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tautomers depending on pH and hydration, several of these bare the distinctive pyrylium core. Asahina, Yasuhiko; Inubuse, Mototaro (1928). "Über die Reduktion...

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Alexandru Balaban

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investigating the synthesis and properties of pyrylium salts. He discovered with co-workers a new way of synthesis of pyrylium salts by diacylation of alkenes. This...

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Stibinin

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stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium Ashe, Arthur J. (December...

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Silabenzene

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germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium Nomenclature of Organic...

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Oxatriquinacene

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them to oxatriquinane. Triethyloxonium tetrafluoroborate Brookhart's acid Pyrylium salt Mark Mascal; Nema Hafezi; Nabin K. Meher & James C. Fettinger (2008)...

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Potential applications of graphene

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hydroxyl-terminated atomic defects that participate in a Grotthuss-type relay, while pyrylium-like ether terminations did not. Recently, Paul and co-workers at IISER...

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Stannabenzene

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germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium Ebrahimi, Arash Afshar;...

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