| Revision as of 16:16, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 454837417 of page 1,2-Dioxin for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 23:00, 23 September 2023 edit Citation bot (talk | contribs)Bots5,407,460 edits Alter: issue. Add: s2cid, authors 1-1. Removed parameters. Formatted dashes. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Hypothetical chemical compounds | #UCB_Category 5/88 |
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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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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 442489175 |
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| verifiedrevid = 477204382 |
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| ImageFile = 1,2-dioxin.svg |
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| ImageFile = 1,2-dioxin.svg |
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| ImageSize = 100 |
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| ImageSize = 100 |
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| ImageName = Skeletal formula of 1,2-dioxin |
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| ImageName = Skeletal formula of 1,2-dioxin |
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| ImageFile1 = 1,2-dioxin-3D-balls.png |
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| ImageFileL1 = 1,2-Dioxin-3D-balls 2.png |
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| ImageFileR1 = 1,2-Dioxin-3D-spacefill.png |
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| ImageSize1 = 100 |
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| ImageName1 = Ball and stick model of 1,2-dioxin |
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| ImageName1 = Ball and stick model of 1,2-dioxin |
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| PIN= 1,2-Dioxine |
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| SystematicName = 1,2-Dioxine<ref>{{Cite web|title = CID 15559065 - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=15559065&loc=ec_rcs|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 7 October 2011|location = USA|date = 12 February 2002|at = Identification and Related Records}}</ref> |
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| SystematicName = 1,2-Dioxacyclohexa-3,5-diene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = <!-- blanked - oldvalue: 289-87-2 --> |
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| CASNo_Ref = {{cascite|changed|??}} |
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| PubChem = 15559065 |
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| CASNo = 289-87-2 |
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| PubChem_Ref = {{Pubchemcite|correct|pubchem}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID = 10606250 |
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| UNII = R8H79L3J69 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = O1OC=CC=C1 |
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| PubChem = 15559065 |
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| ChemSpiderID = 10606250 |
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| StdInChI = 1S/C4H4O2/c1-2-4-6-5-3-1/h1-4H |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = O1OC=CC=C1 |
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| InChI = 1/C4H4O2/c1-2-4-6-5-3-1/h1-4H |
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| StdInChI = 1S/C4H4O2/c1-2-4-6-5-3-1/h1-4H |
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| StdInChIKey = VCZQYTJRWNRPHF-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C4H4O2/c1-2-4-6-5-3-1/h1-4H |
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| InChIKey = VCZQYTJRWNRPHF-UHFFFAOYAH |
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| StdInChIKey = VCZQYTJRWNRPHF-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = VCZQYTJRWNRPHF-UHFFFAOYAH |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 4 |
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| C=4 | H=4 | O=2 |
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| H = 4 |
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| O = 2 |
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| ExactMass = 84.021129372 g mol<sup>-1</sup> |
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}} |
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}} |
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| Section3 = {{Chembox Related |
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|Section3={{Chembox Related |
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| OtherCpds = ]<br /> |
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| OtherCompounds = ]<br /> |
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] |
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] |
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}} |
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}} |
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}} |
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}} |
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{{For|other dioxin compounds|dioxin}} |
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'''1,2-Dioxin''' is a ], ], ]<ref>{{Cite journal |last1=Pelloni |first1=Stefano |last2=Faglioni |first2=Francesco |last3=Lazzeretti |first3=Paolo |date=2013-09-01 |title=Parity violation energies of C4H4X2 molecules for X = O, S, Se, Te and Po |url=https://doi.org/10.1080/00268976.2013.794396 |journal=Molecular Physics |volume=111 |issue=16–17 |pages=2387–2391 |doi=10.1080/00268976.2013.794396 |s2cid=100861633 |issn=0026-8976}}</ref> ] with the ] C{{sub|4}}H{{sub|4}}O{{sub|2}}. It is an ]ic form of ] (or ''p''-dioxin). |
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Due to its ]-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Calculations suggest that it would isomerize rapidly into but-2-enedial.<ref>{{Cite book|last=Matsumoto|first=M.|chapter-url=https://books.google.com/books?id=Ah6GAwAAQBAJ&pg=PA13|title=Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 16: Six-Membered Hetarenes with Two Identical Heteroatoms|publisher=Georg Thieme Verlag|year=2014|isbn=9783131718815|pages=13|chapter=Product Class 1: 1,2-Dioxins and Benzo- and Dibenzo- Fused Derivatives|access-date=2020-06-12}}</ref> Even ] ] are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin.<ref>{{Cite journal | doi = 10.1021/ja00368a021| title = Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide| journal = Journal of the American Chemical Society| volume = 104| issue = 4| pages = 1041| year = 1982| last1 = Smith| first1 = Jimmie P.| last2 = Schrock| first2 = Alan K.| last3 = Schuster| first3 = Gary B.}}.</ref> Indeed, in 1990, 3,6-bis(''p''-tolyl)-1,2-dioxin was wrongly accounted as the first stable derivative.<ref>{{Cite journal | doi = 10.1021/jo00300a026| title = Electron transfer to excited doublet states. Photoirradiation of 10-methylphenothiazine cation radical perchlorate in solutions of phenylacetylene and p-tolylacetylene in acetonitrile| journal = The Journal of Organic Chemistry| volume = 55| issue = 13| pages = 4086| year = 1990| last1 = Shine| first1 = Henry J.| last2 = Zhao| first2 = Da Chuan}}.</ref> It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable ].<ref>{{Cite journal | doi = 10.1021/jo034305i| pmid = 12737603| title = Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study| journal = The Journal of Organic Chemistry| volume = 68| issue = 10| pages = 4108–11| year = 2003| last1 = Block| first1 = Eric| last2 = Shan| first2 = Zhixing| last3 = Glass| first3 = Richard S.| last4 = Fabian| first4 = Jürgen}}</ref> |
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<gallery> |
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File:Dioxin isomers.svg|The isomers 1,2-dioxin (left) and 1,4-dioxin (right) |
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File:1,4-diphenyl-2,3-benzodioxin.svg|Structure of the transient 1,4-diphenyl- 2,3-benzodioxin |
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File:Revised structure 1,2-Dioxin.svg|Dioxin ('''1''') and dione form ('''2''') |
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</gallery> |
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== References == |
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{{Reflist}} |
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{{DEFAULTSORT:Dioxin, 1, 2-}} |
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{{Heterocyclic-stub}} |