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

, a methine group or methine bridge is a trivalent

functional group 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 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 relative abundance of methane ...

. It consists of a

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon ma ...

atom bound by two single

bond Bond or bonds may refer to: Common meanings * Bond (finance), a type of debt security * Bail bond, a commercial third-party guarantor of surety bonds in the United States * Chemical bond, the attraction of atoms, ions or molecules to form chemical ...

s 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 betwee ...

, where one of the single bonds is to a

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...

. The group is also called methyne or methene; 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 (2007
''Methanylylidene group''
in the Chemical Entities of Biological Interest (ChEBI) database. Accessed on 2015-03-05. 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 (). (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 Piperylene or 1,3-pentadiene is an organic compound with the formula . It is a volatile, flammable hydrocarbon. It is one of the five positional isomers of pentadiene. Reactions and occurrence Piperylene is a typical diene. It forms a sul ...

, 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 the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

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 theoretical 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 stability. It is conventionally represented ...

s. When closed, as in

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

, they often give

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

character to the compound.

References

Functional groups Substituents {{Functional Groups

Overlapping methines

See also

References