| 词条 | Ethylene dione |
| 释义 |
| ImageFile = Dicarbon dioxide 3D spacefill.png | ImageSize = 190 | ImageAlt = Ball-and-stick model of ethylene dione | IUPACName = Ethene-1,2-dione | SystematicName = Ethenedione | OtherNames = Dicarbon dioxide Dimeric carbon monoxide Dimeric carbonous oxide Dimeric carbon(II) oxide Ethylenedione |Section1={{Chembox Identifiers | CASNo = 4363-38-6 | PubChem = 314937 | ChemSpiderID = 278619 | SMILES = O=C=C=O | InChI = 1S/C2O2/c3-1-2-4 | InChIKey = FONOSWYYBCBQGN-UHFFFAOYSA-N}} |Section2={{Chembox Properties | C=2 | O=2 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} Ethylene dione or ethylenedione, also called dicarbon dioxide, ethenedione, or ethene-1,2-dione, is a chemical compound with the formula {{chem2|C2O2}} or {{chem2|O\\dC\\dC\\dO}}. It is an oxide of carbon (an oxocarbon), and can be described as the carbon-carbon covalent dimer of carbon monoxide.[1] It can also be thought of as the dehydrated form of glyoxylic acid ({{chem2|H(C\\dO)COOH}}), or a ketone of ethenone {{chem2|H2C\\dC\\dO}}. Synthesis attemptsThe existence of ethylenedione was first suggested in 1913.[2] However, for over a century the compound had eluded all attempts to synthesize and observe it, and it came to be considered a purely hypothetical compound, or at best an "exceedingly coy molecule".[3] In 2015, a research group reported the creation of ethylenedione — by using laser light to eject an electron from the corresponding stable singly-charged anion {{chem2|C2O2(-)}} — and its spectroscopic characterization.[4] However, the reported spectrum was later found to match that of the oxyallyl diradical, {{chem2|(H2C^{•})2CO}}, formed by rearrangement or disproportionation under the high-energy experimental conditions rather than simple electron loss.[5] Theoretical investigationsDespite the existence of the closed-shell Kekulé structure, O=C=C=O, the lowest bound state of ethyledione is a triplet. It would then be a diradical, with an electronic structure motif similar to the oxygen molecule. However, when the molecule is distorted away from its equilibrium geometry, the potential surfaces of the triplet and singlet states intersect, allowing for intersystem crossing to the singlet state, which is unbound and dissociates to two ground-state CO molecules. The timescale of the intersystem crossing was predicted to be 0.5 ns,[6] making triplet ethylenedione a transient, yet spectroscopically long-lived molecule. On the other hand, the monoanion of ethylenedione, OCCO−, as well as the dianion {{chem|C|2|O|2|2-}}, called acetylenediolate, are both stable.[7][8] Recent theoretical computations suggest that the in situ preparation and characterization of ethylenedione may be possible through low-energy free-electron induced single-molecule engineering.[1] Koch's glyoxylideIn the 1940s, Detroit physician William Frederick Koch claimed that he had synthesized this compound, which he called glyoxylide, and that it was an antidote to the toxins that caused a long list of ailments, including diabetes and cancer. The claims were false and the drug was classified as a fraud by the FDA.[9] See also
References1. ^1 {{Cite journal|first1=Daly|last1=Davis|first2=Y.|last2=Sajeev|date=2017-02-22|title=Communication: Low-energy free-electron driven molecular engineering: In situ preparation of intrinsically short-lived carbon-carbon covalent dimer of CO|journal=The Journal of Chemical Physics|volume=146|issue=8|pages=081101|doi=10.1063/1.4976969|issn=0021-9606}} {{Oxides of carbon}}{{Inorganic compounds of carbon}}2. ^H. Staudinger, E. Anthes, Ber. Dtsch. Chem. Ges. 1913, 46, 1426. 3. ^{{Citation |last= Lewars|first=Errol |year=2008 |title=Modeling Marvels |publisher=Springer |chapter=9 – Ethenedione C2O2}} 4. ^Andew R. Dixon, Tian Xue and Andrei Sanov (2015): "Spectroscopy of Ethylenedione", Angewandte Chemie, International Edition, volume 54, issue 30, pages 8764-8767, {{doi|10.1002/anie.201503423}}. 5. ^Katharine G. Lunny, Yanice Benitez, Yishai Albeck, Daniel Strasser, John F. Stanton, Robert E. Continetti (2018): "Spectroscopy of Ethylenedione and Ethynediolide: A Reinvestigation". Angewandte Chemie, International Edition, volume 57, issue 19, pages 5394-5397.{{doi|10.1002/anie.201801848}} 6. ^D. Schröder, C. Heinemann, H. Schwarz, J. N. Harvey, S. Dua, S. J. Blanksby, and John, H. Bowie, "Ethylenedione: An Intrinsically Short-Lived Molecule", Chem. Eur. J., 4, 2550-2557 (1998). 7. ^J. R. Thomas, B. J. DeLeeuw, P. O’Leary, H. F. Schaefer III, B. J. Duke, B. O’Leary "The ethylenedione anion: Elucidation of the intricate potential energy hypersurface", J. Chem. Phys, 102, 6525-6536(1995). 8. ^P. Pyykkö and N. Runeberg, "Ab initio studies of bonding trends: Part 8. The 26-electron A≡B-C≡Dn and the 30-electron A=B=C=Dn systems", J. Mol. Struct. THEOCHEM, 234, 269-277(1991). 9. ^{{cite interview |first= William W. |last= Goodrich |interviewer= Ronald T. Ottes and Fred L. Lofsvold |date= October 15–16, 1986 |url= https://www.fda.gov/downloads/AboutFDA/History/ResearchTeaching/OralHistories/UCM372999.pdf |title= FDA Oral History Interview, Goodrich |page= 31 }} 2 : Oxocarbons|Heterocumulenes |
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