In
chemistry
Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...
, delocalized electrons are
electron
The electron (, or in nuclear reactions) is a subatomic particle with a negative one elementary charge, elementary electric charge. It is a fundamental particle that comprises the ordinary matter that makes up the universe, along with up qua ...
s in a
molecule
A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...
,
ion or solid
metal
A metal () is a material that, when polished or fractured, shows a lustrous appearance, and conducts electrical resistivity and conductivity, electricity and thermal conductivity, heat relatively well. These properties are all associated wit ...
that are not associated with a single
atom
Atoms are the basic particles of the chemical elements. An atom consists of a atomic nucleus, nucleus of protons and generally neutrons, surrounded by an electromagnetically bound swarm of electrons. The chemical elements are distinguished fr ...
or 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 atom ...
.
[IUPAC Gold Boo]
''delocalization''
/ref>
The term delocalization is general and can have slightly different meanings in different fields:
* In 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 ...
, it refers to resonance
Resonance is a phenomenon that occurs when an object or system is subjected to an external force or vibration whose frequency matches a resonant frequency (or resonance frequency) of the system, defined as a frequency that generates a maximu ...
in 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 and aromatic compounds.
* In solid-state physics
Solid-state physics is the study of rigid matter, or solids, through methods such as solid-state chemistry, quantum mechanics, crystallography, electromagnetism, and metallurgy. It is the largest branch of condensed matter physics. Solid-state phy ...
, it refers to free electrons that facilitate electrical conduction
Electrical resistivity (also called volume resistivity or specific electrical resistance) is a fundamental specific property of a material that measures its electrical resistance or how strongly it resists electric current. A low resistivity i ...
.
* In quantum chemistry
Quantum chemistry, also called molecular quantum mechanics, is a branch of physical chemistry focused on the application of quantum mechanics to chemical systems, particularly towards the quantum-mechanical calculation of electronic contributions ...
, it refers to molecular orbital electrons that have extended over several adjacent atoms.
Resonance
In the simple aromatic ring of 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 ...
, the delocalization of six π electrons
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 ...
over the C6 ring is often graphically indicated by a circle. The fact that the six C-C bonds are equidistant is one indication that the electrons are delocalized; if the structure were to have isolated double bonds alternating with discrete single bonds, the bond would likewise have alternating longer and shorter lengths. In valence bond theory
In chemistry, valence bond (VB) theory is one of the two basic theories, along with molecular orbital (MO) theory, that were developed to use the methods of quantum mechanics to explain chemical bonding. It focuses on how the atomic orbitals of ...
, delocalization in benzene is represented by resonance structures.
Electrical conduction
Delocalized electrons also exist in the structure of solid metals. Metallic structure consists of aligned positive ions (cation
An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...
s) in a "sea" of delocalized electrons. This means that the electrons are free to move throughout the structure, and gives rise to properties such as conductivity.
In diamond
Diamond is a Allotropes of carbon, solid form of the element carbon with its atoms arranged in a crystal structure called diamond cubic. Diamond is tasteless, odourless, strong, brittle solid, colourless in pure form, a poor conductor of e ...
all four outer electrons of each 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 are 'localized' between the atoms in covalent bonding. The movement of electrons is restricted and diamond does not conduct an electric current. In graphite
Graphite () is a Crystallinity, crystalline allotrope (form) of the element carbon. It consists of many stacked Layered materials, layers of graphene, typically in excess of hundreds of layers. Graphite occurs naturally and is the most stable ...
, each carbon atom uses only 3 of its 4 outer energy level electrons in covalently bonding to three other carbon atoms in a plane. Each carbon atom contributes one electron to a delocalized system of electrons that is also a part of the chemical bonding. The delocalized electrons are free to move throughout the plane. For this reason, graphite conducts electricity along the planes of carbon atoms, but does not conduct in a direction at right angle
In geometry and trigonometry, a right angle is an angle of exactly 90 Degree (angle), degrees or radians corresponding to a quarter turn (geometry), turn. If a Line (mathematics)#Ray, ray is placed so that its endpoint is on a line and the ad ...
s to the plane.
Molecular orbitals
Standard ab initio quantum chemistry methods lead to delocalized orbitals that, in general, extend over an entire molecule and have the symmetry of the molecule. Localized orbitals may then be found as linear combination
In mathematics, a linear combination or superposition is an Expression (mathematics), expression constructed from a Set (mathematics), set of terms by multiplying each term by a constant and adding the results (e.g. a linear combination of ''x'' a ...
s of the delocalized orbitals, given by an appropriate unitary transformation.
In the methane molecule, ab initio calculations show bonding character in four molecular orbitals, sharing the electrons uniformly among all five atoms. There are two orbital levels, a bonding molecular orbital formed from the 2s orbital on carbon and triply degenerate bonding molecular orbitals from each of the 2p orbitals on carbon. The localized sp3 orbitals corresponding to each individual bond in valence bond theory
In chemistry, valence bond (VB) theory is one of the two basic theories, along with molecular orbital (MO) theory, that were developed to use the methods of quantum mechanics to explain chemical bonding. It focuses on how the atomic orbitals of ...
can be obtained from a linear combination of the four molecular orbitals.
See also
* Aromatic ring current
* Electride
* Solvated electron
References
{{Authority control
Chemical bonding
Electron states