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| Names | |||
|---|---|---|---|
| IUPAC name cyclohexane-1,2,3,4,5,6-hexone | |||
| Other names hexaketocyclohexane, triquinoyl | |||
| Identifiers | |||
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3D model (JSmol) | |||
| ChemSpider |
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| ECHA InfoCard | 100.007.649 | ||
| UNII | |||
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| Properties | |||
| C6O6 | |||
| Molar mass | 168.060 g·mol−1 | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Cyclohexanehexone, also known ashexaketocyclohexane andtriquinoyl, is anorganic compound with formulaC6O6, the sixfoldketone ofcyclohexane. It is anoxide ofcarbon (anoxocarbon), ahexamer ofcarbon monoxide.
The compound is expected to be highly unstable, even less stable than thecyclohexanehexathione analog, and as of 1999 had only been observed as an ionized fragment duringmass spectrometry studies.[1][2]
Cyclohexanehexone can be viewed as the neutral counterpart of therhodizonateanionC6O2−6. The singly charged anionC6O−6 has been detected in mass spectrometry experiments, formed byoligomerization of carbon monoxide through the formation ofmolybdenumcarbonyls.[3]
According toX-ray diffraction analysis, thereagent traded under the name "cyclohexanehexone octahydrate" or equivalent names is actuallydodecahydroxycyclohexane dihydrate—thegeminal diol derivative of the six ketone groups with an additional two molecules of water—a solid that decomposes at 95 °C.[4][5]
In 1966, Howard E. Worne of Natick Chemical Industries patented compounds with formulasC10O8 andC14O10, which can be described as the fusion of two or three molecules ofC6O6, claimed to be produced by the action ofultraviolet radiation on a hot water solution of the parent compound.[6]
In the late 1940s, William J. Hale claimed that "triquinoyl", being atrimer ofWilliam Frederick Koch'sglyoxylide, should be just as effective as the latter against "diabetes, arthritis, poliomyelitis, and even cancer".[7] Even though there is no research supporting this claim (and Koch's glyoxylide preparations were found to be just distilled water),[8] triquinoyl is still listed as an ingredient of somealternative medicine remedies.[9]
