In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal

that are not associated with a single atom or a covalent bond.[1]

The term delocalization is general and can have slightly different meanings in
different fields:

In organic chemistry, it refers to resonance in conjugated systems and aromatic

compounds.
In solid-state physics, it refers to free electrons that facilitate electrical
conduction.
In quantum chemistry, it refers to molecular orbital electrons that have extended
over several adjacent atoms.
Resonance
Main article: Resonance (chemistry)
In the simple aromatic ring of benzene, the delocalization of six π electrons 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, delocalization in benzene is represented by resonance
structures.

Electrical conduction
Main article: Metallic bonding
Delocalized electrons also exist in the structure of solid metals. Metallic
structure consists of aligned positive ions (cations) 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 all four outer electrons of each carbon 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, 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 angles to the plane.

Molecular orbitals
Main article: Molecular orbital
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 combinations 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 can be obtained from a linear combination of the four
molecular orbitals.

See also
Aromatic ring current
Electride
Solvated electron
References
 IUPAC Gold Book delocalization
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Categories: Chemical bondingElectron states
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