| Revision as of 16:15, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,294 edits Saving copy of the {{chembox}} taken from revid 465742449 of page 1,2-Dioxetanedione for the Chem/Drugbox validation project (updated: 'CASNo'). |
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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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| verifiedrevid = 477204215 |
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| Name = |
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| ImageFile = 1,2-Dioxetanedione.svg |
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| ImageFile = 1,2-Dioxetanedione.svg |
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| ImageFile1 = File:Chemfm 1 2 dioxetanedione.svg |
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| ImageSize = 120px |
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| ImageSize = 120px |
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| IUPACName = 1,2-Dioxetane-3,4-dione |
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| PIN = 1,2-Dioxetanedione |
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| OtherNames = Peroxyacid ester |
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| OtherNames = Peroxyacid ester |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| InChIKey = WYNZXNXFHYJUTE-UHFFFAOYAI |
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| InChIKey = WYNZXNXFHYJUTE-UHFFFAOYAI |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C2O4/c3-1-2(4)6-5-1 |
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| StdInChI = 1S/C2O4/c3-1-2(4)6-5-1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WYNZXNXFHYJUTE-UHFFFAOYSA-N |
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| StdInChIKey = WYNZXNXFHYJUTE-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = <!-- blanked - oldvalue: 26974-08-3 --> |
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| CASNo = 26974-08-3 |
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| PubChem = 14833747 |
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| PubChem = 14833747 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 11535432 |
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| ChemSpiderID = 11535432 |
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| SMILES = O=C1OOC1=O |
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| SMILES = O=C1OOC1=O |
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| InChI = 1/C2O4/c3-1-2(4)6-5-1 |
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| InChI = 1/C2O4/c3-1-2(4)6-5-1 |
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| C=2|O=4 |
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| C=2 | O=4 |
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The ] ] '''1,2-dioxetanedione''', or '''1,2-dioxacyclobutane-3,4-dione''', often called '''peroxyacid ester''', is an unstable ] of ] (an ]) with formula C{{sub|2}}O{{sub|4}}. It can be viewed as a double ] of ] (1,2-dioxacyclobutane), or a cyclic ] of carbon dioxide.<ref>Alfred Hassner (1985): Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42. {{ISBN|978-0-471-05624-9}} {{ISBN|978-0-470-18720-3}} John Wiley & Sons.</ref> |
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In ordinary conditions, it quickly decomposes to ] (CO{{sub|2}}) even at {{Convert|180|K|C|sigfig=3}}, but can be detected by ] and other techniques.<ref>{{cite journal|author=Herman F. Cordes|author2=Herbert P. Richter|author3=Carl A. Heller|year=1969|title=Mass spectrometric evidence for the existence of 1,2-dioxetanedione (carbon dioxide dimer). Chemiluminescent intermediate|journal=J. Am. Chem. Soc.|volume=91|issue=25|pages=7209|doi=10.1021/ja01053a065}} |
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</ref><ref>{{cite journal|title=Chemilumineszenz des "Dioxetandions"|trans-title=Chemiluminescence of „Dioxetanedione“|author=J. Stauff|author2=W. Jaeschke|author3=G. Schlögl|year=1972|journal=Z. Naturforsch.|volume=B 27|issue=11|pages=1434–1435|doi=10.1515/znb-1972-1140|s2cid=94708095|doi-access=free|url=http://publikationen.ub.uni-frankfurt.de/files/76112/10.1515_znb-1972-1140.pdf}}</ref> |
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1,2-Dioxetanedione is an intermediate in the ] ]s used in ]s.<ref>{{cite journal|last1=Vacher|first1=Morgane|last2=Fdez. Galván|first2=Ignacio|last3=Ding|first3=Bo-Wen|last4=Schramm|first4=Stefan|last5=Berraud-Pache|first5=Romain|last6=Naumov|first6=Panče|last7=Ferré|first7=Nicolas|last8=Liu|first8=Ya-Jun|last9=Navizet|first9=Isabelle|last10=Roca-Sanjuán|first10=Daniel|last11=Baader|first11=Wilhelm J.|last12=Lindh|first12=Roland|title=Chemi- and Bioluminescence of Cyclic Peroxides|journal=Chemical Reviews|volume=118|issue=15|pages=6927–6974|date=March 2018|doi=10.1021/acs.chemrev.7b00649|pmid=29493234}}</ref><ref>{{cite journal | author = Richard Bos | author2 = Neil W. Barnett | author3 = Gail A. Dyson| author4 = Kieran F. Lim | author5 = Richard A. Russell | author6 = Simon P. Watson | name-list-style = amp | year = 2003 | title = Studies on the mechanism of the peroxyoxalate chemiluminescence reaction: Part 1. Confirmation of 1,2-dioxetanedione as an intermediate using 13C nuclear magnetic resonance spectroscopy | journal = Analytica Chimica Acta | volume = 502 | issue = 2 | doi = 10.1016/j.aca.2003.10.014 | pages = 141–147}} |
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</ref> The decomposition proceeds via a ] ] ] intermediate.<ref>{{cite journal | author = Richard Bos | author2 = Sarah A. Tonkin | author3 = Graeme R. Hanson| author4 = Christopher M. Hindson | author5 = Kieran F. Lim | author6 = Neil W. Barnett | name-list-style = amp | year = 2009 | title = In Search of a Chemiluminescence 1,4-Dioxy Biradical | journal = J. Am. Chem. Soc. | volume = 131 | issue = 8 | pages = 2770–2771 | doi = 10.1021/ja808401p | pmid = 19206238}}</ref> |
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It is an intermediate in a reaction (between ] and ] in ], accumulating in solution at room temperature up to a few ]s, provided that the activating ] and all traces of metals and other ] agents are removed from the system, and the reactions are carried out in an inert atmosphere.<ref name=ciscato>Luiz F. M. L. Ciscato, Fernando H. Bartoloni, Erick L. Bastos, and Wilhelm J. Baader (2009), ''Direct Kinetic Observation of the Chemiexcitation Step in Peroxyoxalate Chemiluminescence''. Journal of Organic Chemistry, volume 74, 8974–8979. {{doi|10.1021/jo901402k}}.</ref> |
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==See also== |
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* ] |
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==References== |
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{{Reflist}} |
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==External links== |
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*{{Commonscatinline}} |
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{{Oxides of carbon}} |
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{{DEFAULTSORT:Dioxetanedione, 1, 2-}} |
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