The chemicalcompound1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula C2O4. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.[1]
In ordinary conditions, it quickly decomposes to carbon dioxide (CO2) even at 180 K (−93.1 °C), but can be detected by mass spectrometry and other techniques.[2][3]
Recently it has been found that a high-energy intermediate in one of these reactions (between oxalyl chloride and hydrogen peroxide in ethyl acetate), which is presumed to be 1,2-dioxetanedione, can accumulate in solution at room temperature (up to a few micromoles at least), provided that the activating dye and all traces of metals and other reducing agents are removed from the system, and the reactions are carried out in an inert atmosphere.[7]
^Alfred Hassner (1985): Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42. ISBN978-0-471-05624-9ISBN978-0-470-18720-3 John Wiley & Sons.
^Herman F. Cordes; Herbert P. Richter; Carl A. Heller (1969). "Mass spectrometric evidence for the existence of 1,2-dioxetanedione (carbon dioxide dimer). Chemiluminescent intermediate". J. Am. Chem. Soc. 91 (25): 7209. doi:10.1021/ja01053a065.
^J. Stauff; W. Jaeschke; G. Schlögl (1972). "Chemilumineszenz des "Dioxetandions"" [Chemiluminescence of „Dioxetanedione“] (PDF). Z. Naturforsch. B 27 (11): 1434–1435. doi:10.1515/znb-1972-1140. S2CID 94708095.
^Vacher, Morgane; Fdez. Galván, Ignacio; Ding, Bo-Wen; Schramm, Stefan; Berraud-Pache, Romain; Naumov, Panče; Ferré, Nicolas; Liu, Ya-Jun; Navizet, Isabelle; Roca-Sanjuán, Daniel; Baader, Wilhelm J.; Lindh, Roland (March 2018). "Chemi- and Bioluminescence of Cyclic Peroxides". Chemical Reviews. 118 (15): 6927–6974. doi:10.1021/acs.chemrev.7b00649. PMID 29493234.
^Richard Bos; Neil W. Barnett; Gail A. Dyson; Kieran F. Lim; Richard A. Russell & Simon P. Watson (2003). "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". Analytica Chimica Acta. 502 (2): 141–147. doi:10.1016/j.aca.2003.10.014.
^Richard Bos; Sarah A. Tonkin; Graeme R. Hanson; Christopher M. Hindson; Kieran F. Lim & Neil W. Barnett (2009). "In Search of a Chemiluminescence 1,4-Dioxy Biradical". J. Am. Chem. Soc. 131 (8): 2770–2771. doi:10.1021/ja808401p. PMID 19206238.
^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.
External linksedit
Media related to 1,2-Dioxetanedione at Wikimedia Commons
April 11, 2024
dioxetanedione, chemical, compound, dioxetanedione, dioxacyclobutane, dione, often, called, peroxyacid, ester, unstable, oxide, carbon, oxocarbon, with, formula, c2o4, viewed, double, ketone, dioxetane, dioxacyclobutane, cyclic, dimer, carbon, dioxide, namespr. The chemical compound 1 2 dioxetanedione or 1 2 dioxacyclobutane 3 4 dione often called peroxyacid ester is an unstable oxide of carbon an oxocarbon with formula C2O4 It can be viewed as a double ketone of 1 2 dioxetane 1 2 dioxacyclobutane or a cyclic dimer of carbon dioxide 1 1 2 Dioxetanedione NamesPreferred IUPAC name 1 2 DioxetanedioneOther names Peroxyacid esterIdentifiersCAS Number 26974 08 3 N3D model JSmol Interactive imageChemSpider 11535432 YPubChem CID 14833747CompTox Dashboard EPA DTXSID80564519InChI InChI 1S C2O4 c3 1 2 4 6 5 1 YKey WYNZXNXFHYJUTE UHFFFAOYSA N YInChI 1 C2O4 c3 1 2 4 6 5 1Key WYNZXNXFHYJUTE UHFFFAOYAISMILES O C1OOC1 OPropertiesChemical formula C 2O 4Molar mass 88 018 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references In ordinary conditions it quickly decomposes to carbon dioxide CO2 even at 180 K 93 1 C but can be detected by mass spectrometry and other techniques 2 3 1 2 Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks 4 5 The decomposition proceeds via a paramagnetic oxalate biradical intermediate 6 Recently it has been found that a high energy intermediate in one of these reactions between oxalyl chloride and hydrogen peroxide in ethyl acetate which is presumed to be 1 2 dioxetanedione can accumulate in solution at room temperature up to a few micromoles at least provided that the activating dye and all traces of metals and other reducing agents are removed from the system and the reactions are carried out in an inert atmosphere 7 See also edit1 3 dioxetanedioneReferences edit 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 amp Sons Herman F Cordes Herbert P Richter Carl A Heller 1969 Mass spectrometric evidence for the existence of 1 2 dioxetanedione carbon dioxide dimer Chemiluminescent intermediate J Am Chem Soc 91 25 7209 doi 10 1021 ja01053a065 J Stauff W Jaeschke G Schlogl 1972 Chemilumineszenz des Dioxetandions Chemiluminescence of Dioxetanedione PDF Z Naturforsch B 27 11 1434 1435 doi 10 1515 znb 1972 1140 S2CID 94708095 Vacher Morgane Fdez Galvan Ignacio Ding Bo Wen Schramm Stefan Berraud Pache Romain Naumov Pance Ferre Nicolas Liu Ya Jun Navizet Isabelle Roca Sanjuan Daniel Baader Wilhelm J Lindh Roland March 2018 Chemi and Bioluminescence of Cyclic Peroxides Chemical Reviews 118 15 6927 6974 doi 10 1021 acs chemrev 7b00649 PMID 29493234 Richard Bos Neil W Barnett Gail A Dyson Kieran F Lim Richard A Russell amp Simon P Watson 2003 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 Analytica Chimica Acta 502 2 141 147 doi 10 1016 j aca 2003 10 014 Richard Bos Sarah A Tonkin Graeme R Hanson Christopher M Hindson Kieran F Lim amp Neil W Barnett 2009 In Search of a Chemiluminescence 1 4 Dioxy Biradical J Am Chem Soc 131 8 2770 2771 doi 10 1021 ja808401p PMID 19206238 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 External links edit nbsp Media related to 1 2 Dioxetanedione at Wikimedia Commons Retrieved from https en wikipedia org w index php title 1 2 Dioxetanedione amp oldid 1195416817, wikipedia, wiki, book, books, library,
