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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.
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.
The theory predicts the molecular orbitals for π-electrons in π-delocalized molecules, such as ethylene, benzene, butadiene, and pyridine. [ 1 ] [ 2 ] [ 3 ] It provides the theoretical basis for Hückel's rule that cyclic, planar molecules or ions with 4 n + 2 {\displaystyle 4n+2} π-electrons are aromatic .
Benzene, the most widely recognized aromatic compound with six delocalized π-electrons (4n + 2, for n = 1). In organic chemistry, Hückel's rule predicts that a planar ring molecule will have aromatic properties if it has 4n + 2 π-electrons, where n is a non-negative integer.
The bond order is equal to the number of bonding electrons minus the number of antibonding electrons, divided by 2. In this example, there are 2 electrons in the bonding orbital and none in the antibonding orbital; the bond order is 1, and there is a single bond between the two hydrogen atoms. [citation needed]
However, in benzene the remaining six bonding electrons are located in three π (pi) molecular bonding orbitals that are delocalized around the ring. Two of these electrons are in an MO that has equal orbital contributions from all six atoms. The other four electrons are in orbitals with vertical nodes at right angles to each other.
Oxidation state is an important index to evaluate the charge distribution within molecules. [2] The most common definition of oxidation state was established by IUPAC, [3] which let the atom with higher electronegativity takes all the bonding electrons and calculated the difference between the number of electrons and protons around each atom to assign the oxidation states.
In quantum chemistry, the electron localization function (ELF) is a measure of the likelihood of finding an electron in the neighborhood space of a reference electron located at a given point and with the same spin.