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In chemistry isomerisation is the process by which one molecule is transformed into another molecule which has exactly the same atoms, but the atoms are rearranged e.g. A-B-C → B-A-C (these related molecules are known as isomers [1]). In some molecules and under some conditions, isomerisation occurs spontaneously. Many isomers are equal or roughly equal in bond energy, and so exist in roughly equal amounts, provided that they can interconvert relatively freely, that is the energy barrier between the two isomers is not too high. When the isomerisation occurs intramolecularly it is considered a rearrangement reaction.
Instances of Isomerization
- Isomerisations in hydrocarbon cracking. This is usually employed in organic chemistry, where fuels, such as pentane, a straight-chain isomer, are heated in the presence of a platinum catalyst (see image). The resulting mixture of straight- and branched-chain isomers then have to be separated. An industrial process is also the isomerisation of n-butane into isobutane.
Nota Bene: the first product should be 2-methylbutane, rather than 2-methylpentane.
- Trans-cis isomerism. In certain compounds an interconversion of cis and trans isomers can be observed, for instance, with maleic acid and with azobenzene often by photoisomerization. An example is the photochemical conversion of the trans isomer to the cis isomer of resveratrol [2]:
- Aldose-ketose isomerism in biochemistry.
- Isomerisations between conformational isomers. These take place without an actual rearrangement for instance inconversion of two cyclohexane conformations
- Fluxional molecules display rapid interconversion of isomers e.g. Bullvalene.
The energy difference between two isomers is called isomerisation energy. Isomerisations with low energy difference both experimental and computational (in parentheses) are endothermic trans-cis isomerisation of 2-butene with 2.6 (1.2) kcal/mol, cracking of isopentane to n-pentane with 3.6 (4.0) kcal/mol or conversion of trans-2-butene to 1-butene with 2.6 (2.4) kcal/mol.[3]
References
- ^ Gold Book definition: Link
- ^ Resveratrol Photoisomerization: An Integrative Guided-Inquiry Experiment Elyse Bernard, Philip Britz-McKibbin, Nicholas Gernigon Vol. 84 No. 7 July 2007 Journal of Chemical Education 1159
- ^ How to Compute Isomerization Energies of Organic Molecules with Quantum Chemical Methods Stefan Grimme, Marc Steinmetz, and Martin Korth J. Org. Chem.; 2007; 72(6) pp 2118 - 2126; (Article) doi:10.1021/jo062446p
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