organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, a methine group or methine bridge is a trivalent

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

, derived formally from

methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The abundance of methane on Earth makes ...

. It consists of a

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atom bound by two single bonds and one

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

, where one of the single bonds is to a

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

. The group is also called methyne or methene, but its

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

systematic name is methylylidene or methanylylidene. This group is sometimes called "methylidyne", however that name belongs properly to either the methylidyne group (connected to the rest of the molecule by a triple bond) or to the

methylidyne radical 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 ...

(the two atoms as a free molecule with dangling bonds). The name "methine" is also widely used in non-systematic nomenclature for the methanetriyl group (IUPAC): a carbon atom with four single bonds, where one bond is to a hydrogen atom (). (2007
''Methanetriyl group''
in the Chemical Entities of Biological Interest (ChEBI) database. Accessed on 2015-03-05.

Overlapping methines

Two or more methine bridges can overlap, forming a chain or ring of carbon atoms connected by alternating single and double bonds, as in piperylene , or the compound Every carbon atom in this molecule is a methine carbon atom, except for three; two that are attached to the two

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

atoms and not to any hydrogen atoms, and the carbon attached to the nitrogen atom, which is attached to two hydrogen atoms (far right). There is a five-carbon-atom poly-methine chain in the center of this molecule. Chains of alternating single and double bonds often form

conjugated system In physical organic chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases Chemical stability, stability. It is Reson ...

s. When closed, as in

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

, they often give

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

character to the compound.

References

Functional groups Substituents {{Functional Groups

Overlapping methines

See also

References