In chemistry, a double bond is a
covalent bond
A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...
between two
atom
Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons.
Every solid, liquid, gas, and ...
s involving four
bonding electrons as opposed to two in a
single bond
In chemistry, a single bond is a chemical bond between two atoms involving two valence electrons. That is, the atoms share one pair of electrons where the bond forms. Therefore, a single bond is a type of covalent bond. When shared, each of th ...
. Double bonds occur most commonly between two carbon atoms, for example in
alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
s. Many double bonds exist between two different elements: for example, in a
carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a ...
group between a carbon atom and an oxygen atom. Other common double bonds are found in
azo compound
Azo compounds are organic compounds bearing the functional group diazenyl (, in which R and R′ can be either aryl or alkyl groups).
IUPAC defines azo compounds as: "Derivatives of diazene (diimide), , wherein both hydrogens are substituted ...
s (N=N),
imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bo ...
s (C=N), and
sulfoxide
In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl () functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. E ...
s (S=O). In a
skeletal formula
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 ...
, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the
equals sign
The equals sign (British English, Unicode) or equal sign (American English), also known as the equality sign, is the mathematical symbol , which is used to indicate equality in some well-defined sense. In an equation, it is placed between two ...
is used for this. Double bonds were first introduced in chemical notation by
Russia
Russia (, , ), or the Russian Federation, is a List of transcontinental countries, transcontinental country spanning Eastern Europe and North Asia, Northern Asia. It is the List of countries and dependencies by area, largest country in the ...
n chemist
Alexander Butlerov
Alexander Mikhaylovich Butlerov (Алекса́ндр Миха́йлович Бу́тлеров; 15 September 1828 – 17 August 1886) was a Russian chemist, one of the principal creators of the theory of chemical structure (1857–1861 ...
.
Double bonds involving carbon are stronger and shorter than
single bond
In chemistry, a single bond is a chemical bond between two atoms involving two valence electrons. That is, the atoms share one pair of electrons where the bond forms. Therefore, a single bond is a type of covalent bond. When shared, each of th ...
s. The
bond order
In chemistry, bond order, as introduced by Linus Pauling, is defined as the difference between the number of bonds and anti-bonds.
The bond order itself is the number of electron pairs (covalent bonds) between two atoms. For example, in diat ...
is two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in
addition reactions of the halogens).
File:Ethene structural.svg, Ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds).
Ethylene i ...
double bond
File:Leuckart-Wallach-Reaktion Aceton.svg, Acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscib ...
double bond
File:Dimethylsulfoxid.svg, Dimethyl sulfoxide
Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds a ...
double bond
File:Trans-diazene-2D.svg, Diazene
Diimide, also called diazene or diimine, is a compound having the formula (NH)2. It exists as two geometric isomers, ''E'' (''trans'') and ''Z'' (''cis''). The term diazene is more common for organic derivatives of diimide. Thus, azobenzene is ...
double bond
Double bonds in alkenes
![Ethylene-CRC-MW-dimensions-2D-Vector](https://upload.wikimedia.org/wikipedia/commons/4/43/Ethylene-CRC-MW-dimensions-2D-Vector.svg)
The type of bonding can be explained in terms of
orbital hybridisation
In chemistry, orbital hybridisation (or hybridization) is the concept of mixing atomic orbitals to form new ''hybrid orbitals'' (with different energies, shapes, etc., than the component atomic orbitals) suitable for the pairing of electrons to f ...
. In
ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds).
Ethylene i ...
each carbon atom has three
sp2 orbitals and one
p-orbital
In atomic theory and quantum mechanics, an atomic orbital is a Function (mathematics), function describing the location and wave-like behavior of an electron in an atom. This function can be used to calculate the probability of finding any electr ...
. The three sp
2 orbitals lie in a plane with ~120° angles. The p-orbital is perpendicular to this plane. When the carbon atoms approach each other, two of the sp
2 orbitals overlap to form a
sigma bond
In chemistry, sigma bonds (σ bonds) are the strongest type of covalent chemical bond. They are formed by head-on overlapping between atomic orbitals. Sigma bonding is most simply defined for diatomic molecules using the language and tools of s ...
. At the same time, the two p-orbitals approach (again in the same plane) and together they form a
pi bond
In chemistry, pi bonds (π bonds) are covalent chemical bonds, in each of which two lobes of an orbital on one atom overlap with two lobes of an orbital on another atom, and in which this overlap occurs laterally. Each of these atomic orbitals ...
. For maximum overlap, the p-orbitals have to remain parallel, and, therefore, rotation around the central bond is not possible. This property gives rise to
cis-trans isomerism. Double bonds are shorter than single bonds because p-orbital overlap is maximized.
Image:Doppelbindung1.png, 2 sp2 orbitals (total of 3 such orbitals) approach to form a sp2-sp2 sigma bond
Image:Doppelbindung2.png, Two p-orbitals overlap to form a pi-bond in a plane parallel to the sigma plane
Image:Ethylene 3D.png, pi bond
In chemistry, pi bonds (π bonds) are covalent chemical bonds, in each of which two lobes of an orbital on one atom overlap with two lobes of an orbital on another atom, and in which this overlap occurs laterally. Each of these atomic orbitals ...
(green) in ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds).
Ethylene i ...
With 133 pm, the ethylene
C=C bond length
In molecular geometry, bond length or bond distance is defined as the average distance between nuclei of two bonded atoms in a molecule. It is a transferable property of a bond between atoms of fixed types, relatively independent of the rest of ...
is shorter than the C−C length in
ethane
Ethane ( , ) is an organic chemical compound with chemical formula . At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petr ...
with 154 pm. The double bond is also stronger, 636
kJ mol−1 versus 368 kJ mol
−1 but not twice as much as the pi-bond is weaker than the sigma bond due to less effective pi-overlap.
In an alternative representation, the double bond results from two overlapping sp
3 orbitals as in a
bent bond
In organic chemistry, a bent bond, also known as a banana bond, is a type of covalent chemical bond with a geometry somewhat reminiscent of a banana. The term itself is a general representation of electron density or configuration resembling a ...
.
Variations
In molecules with alternating double bonds and single bonds, p-orbital overlap can exist over multiple atoms in a chain, giving rise to a
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 as ...
. Conjugation can be found in systems such as
diene
In organic chemistry a diene ( ) (diolefin ( ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nomenclature. ...
s and
enones. In
cyclic molecule
A cyclic compound (or ring compound) is a term for a chemical compound, compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a Ring (chemistry), ring. Rings may vary in size from three to many ...
s, conjugation can lead to
aromaticity
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 saturate ...
. In
cumulene
In organic chemistry, a cumulene is a compound having three or more ''cumulative'' (consecutive) double bonds. They are analogous to allenes, only having a more extensive chain. The simplest molecule in this class is butatriene (), which is also ...
s, two double bonds are adjacent.
Double bonds are common for
period 2 element
A period 2 element is one of the chemical elements in the second row (or period) of the periodic table of the chemical elements. The periodic table is laid out in rows to illustrate recurring (periodic) trends in the chemical behavior of th ...
s
carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
,
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 ...
, and
oxygen
Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...
, and less common with
elements of higher periods. Metals, too, can engage in multiple bonding in a
metal ligand multiple bond.
Group 14 alkene homologs
Double bonded compounds,
alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
homologs, R
2E=ER
2 are now known for all of the heavier
group 14
The carbon group is a group (periodic table), periodic table group consisting of carbon (C), silicon (Si), germanium (Ge), tin (Sn), lead (Pb), and flerovium (Fl). It lies within the p-block.
In modern International Union of Pure and Applied Chem ...
elements. Unlike the alkenes these compounds are not planar but adopt twisted and/or trans bent structures. These effects become more pronounced for the heavier elements. The distannene (Me
3Si)
2CHSn=SnCH(SiMe
3)
2 has a tin-tin bond length just a little shorter than a single bond, a trans bent structure with pyramidal coordination at each tin atom, and readily dissociates in solution to form (Me
3Si)
2CHSn: (stannanediyl, a carbene analog). The bonding comprises two weak donor acceptor bonds, the lone pair on each tin atom overlapping with the empty p orbital on the other.
In contrast, in disilenes each silicon atom has planar coordination but the substituents are twisted so that the molecule as a whole is not planar. In diplumbenes the Pb=Pb bond length can be longer than that of many corresponding single bonds
Plumbenes and stannenes generally dissociate in solution into monomers with bond enthalpies that are just a fraction of the corresponding single bonds. Some double bonds plumbenes and stannenes are similar in strength to hydrogen bonds.
The
Carter-Goddard-Malrieu-Trinquier model can be used to predict the nature of the bonding.
Types of double bonds between atoms
References
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Chemical bonding