| Preferred IUPAC name |
|Systematic IUPAC name|
3D model (JSmol)
|CH, CH•, CH3•|
|Molar mass||13.0186 g mol−1|
|183.04 J K−1 mol−1|
Std enthalpy of
|594.13 kJ mol−1|
| Methyl (CH3) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Methylidyne, or (unsubstituted) carbyne, is an organic compound whose molecule consists of a single hydrogen atom bonded to a carbon atom. It is the parent compound of the carbynes, which can be seen as obtained from it by substitution of other functional groups for the hydrogen.
The carbon atom is left with either one or three unpaired electrons (unsatisfied valence bonds), depending on the molecule's excitation state; making it a radical. Accordingly, the chemical formula can be CH• or CH3• (also written as ⫶CH); each dot representing an unpaired electron. The corresponding systematic names are methylylidene or hydridocarbon(•), and methanetriyl or hydridocarbon(3•). However, the formula is often written simply as CH.
Methylidyne is a highly reactive gas, that is quickly destroyed in ordinary conditions but is abundant in the interstellar medium (and was one of the first molecules to be detected there). 
The trivial name carbyne is the preferred IUPAC name.
Following the substitutive nomenclature, the molecule is viewed as methane with three hydrogen atoms removed, yielding the systematic name "methylidyne".
Following the additive nomenclature, the molecule is viewed as a hydrogen atom bonded to a carbon atom, yielding the name "hydridocarbon".
By default, these names pay no regard to the excitation state of the molecule. When that attribute is considered, the states with one unpaired electron are named "methylylidene" or "hydridocarbon(•)", whereas the excited states with three unpaired electrons are named "methanetriyl" or "hydridocarbon(3•)".
As an odd-electron species, CH is a radical. The ground state is a doublet (X2Π). The first two excited states are a quartet (with three unpaired electrons) (a4Σ−) and a doublet (A2Δ). The quartet lies at 71 kJ/mol above the ground state. 
Reactions of the doublet radical with non-radical species involves insertion or addition:
whereas reactions of the quartet radical generally involves only abstraction:
Methylidyne can bind to metal atoms as tridentate ligand in coordination complexes. An example is methylidynetricobaltnonacarbonyl HCCo
Methylidyne-like species are implied intermediates in the Fischer–Tropsch process, the hydrogenation of CO to produce hydrocarbons. Methylidyne entities are assumed to bond to the catalyst's surface. A hypothetical sequence is: 
The MnCH intermediate has a tridentate methylidine ligand. The methylene ligand (H2C) is then poised couple to CO or to another methylene, thereby growing the C–C chain. 
The methylylidyne group can exhibit both Lewis acidic and Lewis basic character.  Such behavior is only of theoretical interest since it is not possible to produce methylidyne.
In October 2016, astronomers reported that the very basic chemical ingredients of life – the methylidyne radical ⫶CH, the carbon-hydrogen positive ion :CH+, and the carbon ion ⫶C+ – are the result of ultraviolet light from stars, rather than in other ways, such as the result of turbulent events related to supernovas and young stars, as thought earlier.  These results have given new light to the formation of organic compounds in the early development of life on earth.
Methylidyne can be prepared from bromoform. 
In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
A coordination complex consists of a central atom or ion, which is usually metallic and is called the coordination centre, and a surrounding array of bound molecules or ions, that are in turn known as ligands or complexing agents. Many metal-containing compounds, especially those that include transition metals, are coordination complexes.
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.
Methyl is an organic compound with the chemical formula CH•
3. It is a metastable colourless gas, which is mainly produced in situ as a precursor to other hydrocarbons in the petroleum cracking industry. It can act as either a strong oxidant or a strong reductant, and is quite corrosive to metals.
Unsaturated hydrocarbons are hydrocarbons that have double or triple covalent bonds between adjacent carbon atoms. The term "unsaturated" means more hydrogen atoms may be added to the hydrocarbon to make it saturated. The configuration of an unsaturated carbons include straight chain, such as alkenes and alkynes, as well as branched chains and aromatic compounds.
The skeletal formula, or line-angle formula or shorthand formula, of an organic compound is a type of molecular structural formula that serves as a shorthand representation of a molecule's bonding and some details of its molecular geometry. A skeletal formula shows the skeletal structure or skeleton of a molecule, which is composed of the skeletal atoms that make up the molecule. It is represented in two dimensions, as on a piece of paper. It employs certain conventions to represent carbon and hydrogen atoms, which are the most common in organic chemistry.
A substituent is one or a group of atoms that replaces atoms, thereby becoming a moiety in the resultant (new) molecule.
In organic chemistry, a methine group or methine bridge is a trivalent functional group =CH−, derived formally from methane. It consists of a carbon atom bound by two single bonds and one double bond, where one of the single bonds is to a hydrogen. The group is also called methyne or methene; its IUPAC systematic name is methylylidene or methanylylidene
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is R−:C−R' or R=C: where the R represents substituents or hydrogen atoms.
In chemistry, a nitrene or imene is the nitrogen analogue of a carbene. The nitrogen atom is uncharged and univalent, so it has only 6 electrons in its valence level—two covalent bonded and four non-bonded electrons. It is therefore considered an electrophile due to the unsatisfied octet. A nitrene is a reactive intermediate and is involved in many chemical reactions. The simplest nitrene, HN, is called imidogen, and that term is sometimes used as a synonym for the nitrene class.
In organic chemistry, a carbyne is a general term for any compound whose structure consists of an electrically neutral carbon atom connected by a single covalent bond and has three non-bonded electrons. The carbon atom has either one or three unpaired electrons, depending on its excitation state; making it a radical. The chemical formula can be written R−C· or R−C3·, or just CH.
A transition metal carbene complex is an organometallic compound featuring a divalent organic ligand. The divalent organic ligand coordinated to the metal center is called a carbene. Carbene complexes for almost all transition metals have been reported. Many methods for synthesizing them and reactions utilizing them have been reported. The term carbene ligand is a formalism since many are not derived from carbenes and almost none exhibit the reactivity characteristic of carbenes. Described often as M=CR2, they represent a class of organic ligands intermediate between alkyls (−CR3) and carbynes (≡CR). They feature in some catalytic reactions, especially alkene metathesis, and are of value in the preparation of some fine chemicals.
In chemistry, a reaction intermediate or an intermediate is a molecular entity that is formed from the reactants but is consumed in further reactions in stepwise chemical reactions that contain multiple elementary steps. Intermediates are the reaction product of one elementary step, but do not appear in the chemical equation for an overall chemical equation.
In spectroscopy and quantum chemistry, the multiplicity of an energy level is defined as 2S+1, where S is the total spin angular momentum. States with multiplicity 1, 2, 3, 4, 5 are respectively called singlets, doublets, triplets, quartets and quintets.
Mass spectral interpretation is the method employed to identify the chemical formula, characteristic fragment patterns and possible fragment ions from the mass spectra. Mass spectra is a plot of relative abundance against mass-to-charge ratio. It is commonly used for the identification of organic compounds from electron ionization mass spectrometry. Organic chemists obtain mass spectra of chemical compounds as part of structure elucidation and the analysis is part of many organic chemistry curricula.
In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spontaneously dimerize. Most organic radicals have short lifetimes.
Methylene is an organic compound with the chemical formula CH
2. It is a colourless gas that fluoresces in the mid-infrared range, and only persists in dilution, or as an adduct.
In organic chemistry, a methylidyne group or just methylidyne is a neutral part of a molecule with formula ≡CH, consisting of a carbon atom bonded to a hydrogen atom by one single bond and to the rest of the molecule by one triple bond. For example, a methylidyne group is present in n-methylidyne-1-hexanaminium, H3C−(CH2)5−N+≡CH.