Quinone
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Benzoquinone, or quinone is one of the two isomers of cyclohexadienedione. These compounds have the molecular formula C6H4O2. Orthobenzoquinone is the 1,2-dione, whereas parabenzoquinone is the 1,4-dione.
Orthobenzoquinone is the oxidized form of catechol (1,2-dihydroxybenzene), while parabenzoquinone is the oxidized form of hydroquinone. An acidic potassium iodide solution reduces a solution of benzoquinone to hydroquinone, which is oxidized back with a solution of silver nitrate.
Quinone is also the name for the class of compounds containing either benzoquinone isomers as part of their structure. Quinones are not aromatic, but are diketones.
Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). Others serve as electron acceptors in electron transport chains such as those in Photosystems I & II of photosynthesis, and aerobic respiration. A natural example of the oxidization of hydroquinone to quinone is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterrent in the animal world. Quinones can be partially reduced to quinols.
Benzoquinone is used in organic chemistry as an oxidizing agent. Stronger quinone oxidising agents exist; for instance: 2,3,5,6-tetrachloro-parabenzoquinone (also known as p-chloranil) and 2,3-dicyano-5,6-dichloro-parabenzoquinone (also known as DDQ).
Orthobenzoquinone is the oxidized form of catechol (1,2-dihydroxybenzene), while parabenzoquinone is the oxidized form of hydroquinone. An acidic potassium iodide solution reduces a solution of benzoquinone to hydroquinone, which is oxidized back with a solution of silver nitrate.
Quinone is also the name for the class of compounds containing either benzoquinone isomers as part of their structure. Quinones are not aromatic, but are diketones.
Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). Others serve as electron acceptors in electron transport chains such as those in Photosystems I & II of photosynthesis, and aerobic respiration. A natural example of the oxidization of hydroquinone to quinone is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterrent in the animal world. Quinones can be partially reduced to quinols.
Benzoquinone is used in organic chemistry as an oxidizing agent. Stronger quinone oxidising agents exist; for instance: 2,3,5,6-tetrachloro-parabenzoquinone (also known as p-chloranil) and 2,3-dicyano-5,6-dichloro-parabenzoquinone (also known as DDQ).
