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Concept
Quinone
Summary
The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully conjugated cyclic dione structure".
The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone" (thus the name of the class). Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.
The name is derived from that of quinic acid (with the suffix "-one" indicating a ketone), since it is one of the compounds obtained upon oxidation of quinic acid. Quinic acid, like quinine is obtained from cinchona bark, called quinaquina in the indigenous languages of Peruvian tribes.
Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. (Quinones are conjugated but not aromatic). Quinones are electrophilic Michael acceptors stabilised by conjugation. Depending on the quinone and the site of reduction, reduction can either rearomatise the compound or break the conjugation. Conjugate addition nearly always breaks the conjugation.
File:orthobenzoquinone.svg|[[1,2-Benzoquinone]]
File:P-Benzochinon.svg|[[1,4-Benzoquinone]]
File:1,4-Naphthoquinone.svg|[[1,4-Naphthoquinone]]
File:Anthrachinon.svg|[[anthraquinone|9,10-Anthraquinone]]
The term quinone is also used more generally for a large class of compounds formally derived from aromatic quinones through replacement of some hydrogen atoms by other atoms or radicals.
File:2,3,5,6-tetrachloro-parabenzoquinone.svg|[[Chloranil]], a reagent in organic chemistry
File:HNQ.svg|[[Lawsone]], a dye present in the leaves of the henna plant
File:Alizaryna.svg|[[Alizarin]], a common red dye
File:Dichlorodicyanobenzoquinone.
Official source
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