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Disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation states. Although not widely accepted, disproportionation is sometimes used to describe any desymmetrizing reaction of the following type: 2 A -> A' + A", regardless of any redox process.
The reverse of disproportionation, when a compound in an intermediate oxidation state is formed from precursors of lower and higher oxidation states, is called comproportionation, also known as synproportionation.
The first disproportionation reaction to be studied in detail was:
The chlorine gas reactant is in oxidation state 0. In the products, the chlorine in the Cl- ion has an oxidation number of -1, having been reduced, whereas the oxidation number of the chlorine in the ClO3− ion is +5, indicating that it has been oxidized.
Bromine fluoride undergoes disproportionation reaction to form bromine trifluoride and bromide:
The dismutation of pyruvic acid in other small organic molecules (ethanol + CO2, or lactate and acetate, depending on the environmental conditions) is also an important step in fermentation reactions. Fermentation reactions can also be considered as disproportionation or dismutation biochemical reactions. Indeed, the donor and acceptor of electrons in the redox reactions supplying the chemical energy in these complex biochemical systems are the same organic molecules simultaneously acting as reductant or oxidant.
While in respiration electrons are transferred from substrate (electron donor) to an electron acceptor, in fermentation part of the substrate molecule itself accepts the electrons. Fermentation is therefore a type of disproportionation, and does not involve an overall change in oxidation state of the substrate. Most of the fermentative substrates are organic molecules. However, a rare type of fermentation may also involve the disproportionation of inorganic sulfur compounds in certain sulfate-reducing bacteria.