Tricarbon monoxide
Names | |
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Preferred IUPAC name
3-Oxopropa-1,2-dien-1-ylidene | |
Other names
3-Oxopropadienylidene
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Identifiers | |
3D model (
JSmol ) |
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PubChem CID
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Properties | |
C3O | |
Molar mass | 52.032 g·mol−1 |
Appearance | Gas |
Related compounds | |
Related oxides
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carbon monoxide dicarbon monoxide tetracarbon monoxide |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tricarbon monoxide C3O is a reactive
Natural occurrence
C3O has been detected by its microwave spectrum in the dark cold
The route to produce this is speculated to be:[6]
- HC+
3 + CO2 → HC3O+ + CO - HC3O+ → C3O + H+
or[5]
- C2 + CO → C3O which is more favourable at lower temperatures.
The related C3S is more abundant in dark molecular clouds, even though oxygen is 20 times more common than sulfur. The difference is due to the higher rate of formation and that C3S is less polar.[5]
Production
C3O can be produced by heating Meldrum's acid. This also produces acetone, carbon monoxide and carbon dioxide.[7]
R. L. DeKock and W. Waltner were the first to identify C3O by reacting atomic carbon with carbon monoxide in an argon matrix. They observed an infrared absorption line at 2241 cm−1.[7] They produced carbon atoms by heating graphite inside a thin tantalum tube.[8]
M. E. Jacox photolysed C3O2 in an argon matrix to produce C3O with an IR absorption line at 2244 cm−1, however he did not recognise what was produced.[8]
By heating diazocyclopentanetrione or a similar acid anhydride, (2,4-azo-3-oxo-dipentanoic anhydride), C3O is produced. Also the action of light on tetracarbon dioxide yields C3O and CO.[9]
Heating fumaryl chloride also yields C3O.[3] Heating Lead 2,4-dinitroresorcinate also produces C3O along with C2O, CO and carbon suboxide.[10] An electric discharge in carbon suboxide produces about 11 ppm C3O.[11]
Roger Brown heated 3,5-dimethyl-1-propynolpyrazole to over 700 °C to make C3O.[12] Also pyrolysis of 5,5'-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxanylidene or di-isopropylidene ethylenetetracarboxylate yields C3O.[12]
Irradiating carbon monoxide ice with electrons yields a mixture of carbon oxides, including C3O. This process could happen on icy bodies in space.[13]
Reactions
C3O can be stabilised as a ligand in the pentacarbonyls of group 6 elements as in Cr(CO)5CCCO. This is formed from [n-Bu4N][CrI(CO)5] and the silver acetylide derivative of sodium propiolate (AgC≡CCOONa), and then
C3O deposits a reddish-black film on glass.[12]
The reaction of C3O and
Properties
The C3O molecules do not last long. At the low pressure of 1 pascal, they survive about one second.[18] The force constants for the bonds are: C1-O 14.94, C1-C2 1.39 C2-C3 6.02 mdyn/Å.[8] The bond lengths are C-O 1.149, C1-C2 1.300, C2-C3 1.273 Å. The molecule is linear.[6]
bond | atom 1 | atom 2 | length Å[6] |
force constant mdyn/Å[8] |
IR bands cm−1 |
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CCC-O | C1 | O | 1.149 | 14.94 | |
CC-CO | C2 | C1 | 1.300 | 1.39 | |
C-CCCO | C3 | C2 | 1.273 | 6.02 |
Proton affinity is 885 kJmol−1.[6] The dipole moment is 2.391 D.[14] The oxygen end has a positive charge, and the carbon end the negative charge.[6] The molecule behaves as if there are triple bonds at each end, and a single bond in the middle. This is isoelectronic to cyanogen.[19]
Molecular constants used in determining the microwave spectrum are rotational constant B0=4810.8862 MHz centrifugal distortion constant D0=0.00077 MHz. Known microwave spectral lines vary from 9621.76 for J=1←0 to 182792.35 MHz for J=19←18.[11]
References
- .
- doi:10.1086/186284.
- ^ a b Ruppel, Raimund (1999). "Neue Heterokumulene und Carbene" (PDF) (in German). Gießen: Justus-Liebig-Universität: 13. Retrieved 10 November 2016.
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- ^ S2CID 124813337.
- ^ doi:10.1063/1.455787.
- ^
- ^ .
- .
- .
- ^ .
- ^ .
- doi:10.1086/499245.
- ^ ISBN 978-3642047213.
- .
- PMID 21400561.
- PMID 22120518.
- ^ Information, Reed Business (9 May 1985). "Theory predicts a new oxide of carbon". New Scientist (1455): 21. Retrieved 10 November 2016.
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