Ethylene dione
Names | |
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IUPAC name
Ethene-1,2-dione
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Systematic IUPAC name
Ethenedione | |
Other names
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C2O2 | |
Molar mass | 56.020 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethylene dione or ethylenedione, also called dicarbon dioxide, Carbon peroxide, ethenedione, or ethene-1,2-dione, is a
dimer of carbon monoxide.[1] It can also be thought of as the dehydrated form of glyoxylic acid (H(C=O)COOH), or a ketone of ethenone
H2C=C=O.
Synthesis attempts
The existence of ethylenedione was first suggested in 1913.hypothetical compound, or at best an "exceedingly coy molecule".[3]
In 2015, a research group reported the creation of ethylenedione — by using
anion C2O−2 — and its spectroscopic characterization.[4] However, the reported spectrum was later found to match that of the oxyallyl diradical, (H2C•)2CO, formed by rearrangement or disproportionation under the high-energy experimental conditions rather than simple electron loss.[5]
Theoretical investigations
Despite the existence of the
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 mono
anion of ethylenedione, OCCO−, as well as the dianion C
2O2−
2, called acetylenediolate, are both stable.[7][8]
2O2−
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 glyoxylide
In the 1940s,
FDA.[9]
See also
- Cyclohexanehexone C6O6, also called triquinoyl, formally a trimer of ethylene dione.
- Oxocarbons
References
- ^ PMID 28249449.
- ^ H. Staudinger, E. Anthes, Ber. Dtsch. Chem. Ges. 1913, 46, 1426.
- Bibcode:2008moma.book.....L
- .
- ^ 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).
- ^ 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).
- ^ 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).
- ^ Goodrich, William W. (October 15–16, 1986). "FDA Oral History Interview, Goodrich" (PDF) (Interview). Interviewed by Ronald T. Ottes and Fred L. Lofsvold. p. 31.