| Revision as of 17:06, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 434807808 of page 2,5-Dihydroxy-1,4-benzoquinone for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 07:25, 15 April 2024 edit حسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Hydroquinones using HotCat |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 477211505 |
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| ImageFileL1 = 2,5-dihydroxy-1,4-benzoquinone.svg |
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| ImageFileL1 = 2,5-dihydroxy-1,4-benzoquinone.svg |
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| ImageSizeL1 = 120px |
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| ImageNameL1 = Skeletal formula of 2,5-dihydroxy-1,4-benzoquinone |
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| ImageNameL1 = Skeletal formula of 2,5-dihydroxy-1,4-benzoquinone |
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| ImageFileR1 = 2,5-dihydroxy-1,4-benzoquinone-3D-balls.png |
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| ImageFileR1 = 2,5-dihydroxy-1,4-benzoquinone-3D-balls.png |
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| ImageSizeR1 = 130px |
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| ImageNameR1 = Ball-and-stick model of 2,5-dihydroxy-1,4-benzoquinone |
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| ImageNameR1 = Ball-and-stick model of 2,5-dihydroxy-1,4-benzoquinone |
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| IUPACName = 2,5-dihydroxycyclohexa-2,5-diene-1,4-dione |
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| PIN = 2,5-Dihydroxycyclohexa-2,5-diene-1,4-dione |
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| OtherNames = 2,5-Dihydroxy-p-benzoquinone |
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| OtherNames = 2,5-Dihydroxy-''p''-benzoquinone, anilic acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 62426 |
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| ChemSpiderID = 62426 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = QFSYADJLNBHAKO-UHFFFAOYSA-N |
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| StdInChIKey = QFSYADJLNBHAKO-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 615-94-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 0KG5HVB52Z |
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| PubChem = 69213 |
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| PubChem = 69213 |
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| SMILES = C1=C(C(=O)C=C(C1=O)O)O }} |
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| SMILES = C1=C(C(=O)C=C(C1=O)O)O }} |
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| Section2 = {{Chembox Properties |
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| C=6|H=4|O=4 |
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| Formula = C<sub>6</sub>H<sub>4</sub>O<sub>4</sub> |
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| MolarMass = 140.1 g/mol |
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| MeltingPtC = 212.5 |
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| MeltingPt_ref = <ref name=singh/> |
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'''2,5-Dihydroxy-1,4-benzoquinone''' or '''2,5-dihydroxy-''para''-benzoquinone''' is an organic compound with formula {{chem|C|6|H|4|O|4}}, formally derived from ] by replacing two ] atoms with ] (OH) groups. It is one of seven ] isomers. It is a yellow solid<ref name=singh>Onkar Singh, Aran Kumar, and Karan Singh (2012), . International Journal of Scientific and Research Publications, volume 2, issue 9 |
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ISSN 2250-3153</ref> with planar molecules<ref>Semmingsen, Dag "The crystal and molecular structure of 2,5-dihydroxy-1,4-benzoquinone at -162°C" Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry 1977, volume B31, 11-14.</ref> that exhibits ] properties.<ref>Horiuchi, Sachio; Kumai, Reiji; Tokura, Yoshinori "Hydrogen-bonded donor-acceptor compounds for organic ferroelectric materials" Chemical Communications 2007, 2321-2329. {{doi|10.1039/B617881B}}</ref> |
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The compound is a weak ]: one or both hydroxyls can lose a proton to yield the ]s {{chem|C|6|H|3|O|4|-}} (pK<sub>a1</sub> = 2.95) and {{chem|C|6|H|2|O|4|2-}} (pK<sub>a2</sub> = 4.87), respectively. The latter forms a variety of ]es, functioning as a binucleating ligand.<ref>Kitagawa, Susumu; Kawata, Satoshi "Coordination compounds of 1,4-dihydroxybenzoquinone and its homologues. Structures and properties" Coordination Chemistry Reviews 2002, volume 224, 11-34. {{doi|10.1016/S0010-8545(01)00369-1}}</ref> |
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The compound has been identified as partly responsible for the color of aged ] materials.<ref>Hosoya, Takashi; French, Alfred D.; Rosenau, Thomas "Chemistry of 2,5-dihydroxy--benzoquinone, a key chromophore in aged cellulosics" Mini-Reviews in Organic Chemistry 2013, volume 10, pp. 309-315.</ref> |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Dihydroxy-1,4-benzoquinone, 2,5-}} |
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] |
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] |
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] |
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{{ketone-stub}} |