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Methenium

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(Redirected fromMethyl cation)

Ion of carbon with three hydrogens

Not to be confused withmethanium, a cation with the formulaCH+5.

Methenium

Names

Preferred IUPAC name

Methylium^[1]

Other names

Methyl cation; Carbanylium

Identifiers

CAS Number

14531-53-4^Y

3D model (JSmol)

Interactive image

Beilstein Reference

1839325

ChEBI

CHEBI:29437

ChemSpider

559136

Gmelin Reference

48893

PubChem CID

644094

UNII

IM9JMM7N0Y^Y

CompTox Dashboard(EPA)

DTXSID301319120

InChI

InChI=1S/CH3/h1H3/q+1
Key: JUHDUIDUEUEQND-UHFFFAOYSA-N

SMILES

[CH3+]

Properties

Chemical formula

CH₃⁺

Molar mass

15.034 g·mol⁻¹

Related compounds

Relatedisoelectronic

borane

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Inorganic chemistry,methenium (also calledmethylium,carbenium,^[2]methyl cation, orprotonated methylene) is acation with the formulaCH⁺
₃. It can be viewed as amethylene radical (:CH
₂) with an addedproton (H⁺
), or as amethyl radical (•CH
₃) with oneelectron removed. It is acarbocation and anenium ion, making it the simplest of thecarbenium ions.^[3]

Structure

[edit]

Experiments and calculations generally agree that the methenium ion is planar, with threefoldsymmetry.^[3] The carbon atom is a prototypical (and exact) example of sp² hybridization.

Preparation and reactions

[edit]

Formass spectrometry studies at low pressure, methenium can be obtained byultraviolet photoionization of methyl radical,^[3] or by collisions of monatomic cations such asC⁺
andKr⁺
with neutral methane.^[4] In such conditions, it will react withacetonitrileCH
₃CN to form the ion(CH
₃)
₂CN⁺
.^[5]

Upon capture of a low-energy electron (less than1 eV), it will spontaneously dissociate.^[6]

It is seldom encountered as an intermediate in the condensed phase. It is proposed as a reactive intermediate that forms upon protonation or hydride abstraction of methane withFSO₃H-SbF₅. The methenium ion is very reactive, even towardsalkanes.^[7]

Detection

[edit]

Main article:List of interstellar and circumstellar molecules

Origins of life

[edit]

Main article:Abiogenesis

In June 2023, astronomersdetected, for the first time outside the Solar System, methyl cation, CH₃⁺ (and/orcarbon cation, C⁺), the known basic ingredients oflife, ininterstellar space.^[8]^[9]

References

[edit]

^International Union of Pure and Applied Chemistry (2014).Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013.The Royal Society of Chemistry. p. 1089.doi:10.1039/9781849733069.ISBN 978-0-85404-182-4.
^"Ions, Free Radicals, and Radical-Ion",Nomenclature of Organic Compounds, Advances in Chemistry, vol. 126, AMERICAN CHEMICAL SOCIETY, June 1974, pp. 216–224,doi:10.1021/ba-1974-0126.ch028,ISBN 978-0-8412-0191-0
^^a ^b ^cGolob, L.; Jonathan, N.; Morris, A.; Okuda, M.; Ross, K.J. (1972). "The first ionization potential of the methyl radical as determined by photoelectron spectroscopy".Journal of Electron Spectroscopy and Related Phenomena.1 (5). Elsevier BV:506–508.doi:10.1016/0368-2048(72)80022-7.ISSN 0368-2048.
^Sharma, R. B.; Semo, N. M.; Koski, W. S. (1987). "Dynamics of the reactions of methylium, methylene radical cation, and methyliumylidene with acetylene".The Journal of Physical Chemistry.91 (15). American Chemical Society (ACS):4127–4131.doi:10.1021/j100299a037.ISSN 0022-3654.
^McEwan, Murray J.; Denison, Arthur B.; Huntress, Wesley T.; Anicich, Vincent G.; Snodgrass, J.; Bowers, M. T. (1989). "Association reactions at low pressure. 2. The methylium/methyl cyanide system".The Journal of Physical Chemistry.93 (10). American Chemical Society (ACS):4064–4068.doi:10.1021/j100347a039.ISSN 0022-3654.
^Bahati, E. M.; Fogle, M.; Vane, C. R.; Bannister, M. E.; Thomas, R. D.; Zhaunerchyk, V. (2009-05-11). "Electron-impact dissociation ofCD⁺
₃ andCH⁺
₃ ions producingCD⁺
₂,CH⁺
andC⁺
fragment ions".Physical Review A.79 (5) 052703. American Physical Society (APS).doi:10.1103/physreva.79.052703.ISSN 1050-2947.
^Hogeveen, H.; Lukas, J.; Roobeek, C. F. (1969). "Trapping of the methyl cation by carbon monoxide; formation of acetic acid from methane".Journal of the Chemical Society D: Chemical Communications (16): 920.doi:10.1039/c29690000920.ISSN 0577-6171.
^Sauers, Elisha (27 June 2023)."Webb telescope just found something unprecedented in the Orion Nebula - Astronomers are excited about the detection of a special molecule in space".Mashable.Archived from the original on 27 June 2023. Retrieved27 June 2023.
^Berné, Olivier; et al. (26 June 2023)."Formation of the Methyl Cation by Photochemistry in a Protoplanetary Disk".Nature.621 (7977):56–59.arXiv:2401.03296.doi:10.1038/s41586-023-06307-x.hdl:1887/3716674.PMID 37364766.S2CID 259260435.Archived from the original on 27 June 2023. Retrieved27 June 2023.

Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Imidogen Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur mononitride Sulfur monoxide Titanium(II) oxide
Triatomic	Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene Methylidynephosphane N₂H⁺ Nitrous oxide Nitroxyl Ozone Potassium cyanide Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Trihydrogen cation Water
Four atoms	Acetylene Ammonia Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methyl cation Methyl radical Methylene amidogen Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thiocyanic acid Thioformaldehyde Tricarbon monosulfide Tricarbon monoxide
Five atoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Six atoms	Acetonitrile Cyanobutadiynyl radical Cyclopropenone Diacetylene E-Cyanomethanimine Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methyl isocyanate Methylamine Propyne Vinyl alcohol
Eight atoms	Acetic acid Acrolein Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methyl formate Methylcyanoacetylene
Nine atoms	Acetamide Cyanohexatriyne Dimethyl ether Ethanethiol Ethanol Methyldiacetylene N-Methylformamide Octatetraynyl radical Propene Propionitrile
Ten atoms or more	Acetone Benzene Benzonitrile Buckminsterfullerene (C₆₀, C₆₀⁺, fullerene, buckyball) Butyronitrile C₇₀ fullerene Cyanodecapentayne Ethyl formate Ethylene glycol Heptatrienyl radical Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Pyrimidine