Methyl group
In
3). The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.[1]
Methyl cation, anion, and radical
Methyl cation
The methylium cation (CH+3) exists in the
- CH3OH + H+ → [CH3OH2]+
Similarly,
The methyl cation has been detected in
Methyl anion
The methanide anion (CH−3) exists only in rarefied gas phase or under exotic conditions. It can be produced by electrical discharge in
In discussing mechanisms of organic reactions,
- 2 M + CH3X → MCH3 + MX
where M is an alkali metal.
Methyl radical
The methyl
Reactivity
The reactivity of a methyl group depends on the adjacent substituents. Methyl groups can be quite unreactive. For example, in organic compounds, the methyl group resists attack by even the strongest acids.
Oxidation
The
Methylation
Demethylation (the transfer of the methyl group to another compound) is a common process, and
Deprotonation
Certain methyl groups can be deprotonated. For example, the acidity of the methyl groups in acetone ((CH3)2CO) is about 1020 times more acidic than methane. The resulting carbanions are key intermediates in many reactions in organic synthesis and biosynthesis. Fatty acids are produced in this way.
Free radical reactions
When placed in
Chiral methyl
In the special case where one hydrogen is replaced by
Rotation
A methyl group may rotate around the R−C axis. This is a free rotation only in the simplest cases like gaseous
Etymology
French chemists
Methyl is the IUPAC nomenclature of organic chemistry term for an alkane (or alkyl) molecule, using the prefix "meth-" to indicate the presence of a single carbon.
See also
- AdoMet
- Methylation
References
- ISBN 0-471-60180-2.
- ^ 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. Retrieved 27 June 2023.
- from the original on 27 June 2023. Retrieved 27 June 2023.
- PMID 30034765.
- PMID 12797825.
- S2CID 106409337.
- ^ Thauer, R. K., "Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson", Microbiology, 1998, volume 144, pages 2377–2406.
- PMID 29743234.
- ISSN 0890-9369.
- ^ "Archived copy" (PDF). Archived from the original (PDF) on 2010-07-14. Retrieved 2013-11-26.
{{cite web}}
: CS1 maint: archived copy as title (link) - ^ Heinz G. Floss, Sungsook Lee "Chiral methyl groups: small is beautiful" Acc. Chem. Res., 1993, volume 26, pp 116–122.
- ^ Press,W: Single-particle rotation in molecular crystals (Springer tracts in modern physics 92), Springer: Berlin (1981).
- ^ J. Dumas and E. Péligot (1835) "Mémoire sur l'espirit de bois et sur les divers composés ethérés qui en proviennent" (Memoir on spirit of wood and on the various ethereal compounds that derive therefrom), Annales de chimie et de physique, 58 : 5-74; from page 9: Nous donnerons le nom de méthylène (1) à un radical … (1) μεθυ, vin, et υλη, bois; c'est-à-dire vin ou liqueur spiritueuse du bois. (We will give the name "methylene" (1) to a radical … (1) methy, wine, and hulē, wood; that is, wine or spirit of wood.)
- ^ Note that the correct Greek word for the substance "wood" is xylo-.