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Quinone
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==Properties== Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with [[electron-donating group|electron-donating substituents]] such as [[phenols]] and [[catechol]]s, 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 acceptor]]s 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. <gallery class="skin-invert-image"> 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]] </gallery> 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. <gallery class="skin-invert-image">> 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.svg|[[2,3-Dichloro-5,6-dicyano-1,4-benzoquinone|DDQ]], a reagent in organic chemistry File:Daunorubicin2DACS.svg|[[Daunorubicin]], an anticancer drug </gallery>
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