Isomerization Reaction
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In
chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...
, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...
with a different chemical structure.
Enolization In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The t ...
is an example of isomerization, as is
tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...
ization. When the isomerization occurs intramolecularly it may be called a
rearrangement reaction In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another ...
. When the activation energy for the isomerization reaction is sufficiently small, both isomers will exist in a temperature-dependent equilibrium with each other. Many values of the standard free energy difference, \Delta G^\circ, have been calculated, with good agreement between observed and calculated data.


Examples and applications


Alkanes

Skeletal isomerization occurs in the cracking process, used in the petrochemical industry. As well as reducing the average chain length, straight-chain hydrocarbons are converted to branched isomers in the process, as illustrated the following reaction of ''n''-butane to ''i''-butane. :\overset -> \overset Fuels containing branched hydrocarbons are favored for internal combustion engines for their higher
octane rating An octane rating, or octane number, is a standard measure of a fuel's ability to withstand compression in an internal combustion engine without detonating. The higher the octane number, the more compression the fuel can withstand before detonating ...
.


Alkenes

Terminal alkenes isomerize to internal alkenes in the presence of metal catalysts. This process is employed in the Shell higher olefin process to convert alpha-olefins to internal olefins, which are subjected to olefin metathesis. In certain kinds of alkene polymerization reactions, chain walking is an isomerization process that introduces branches into growing polymers. The ''trans'' isomer of
resveratrol Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources ...
can be converted to the ''cis'' isomer in a photochemical reaction. : Thermal rearrangement of azulene to
naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08  ppm by mass. As an aromati ...
has been observed.


Other examples

Aldose-ketose isomerism, aka Lobry de Bruyn–van Ekenstein transformation, provides an example in saccharide chemistry. : An example of an organometallic chemistry, organometallic isomerization is the production of decaphenylferrocene, from its linkage isomer.


See also

*Base-promoted epoxide isomerization *Epimerization *Racemization *Tautomerization *Linkage isomerism


References

{{Reaction mechanisms Chemical reactions