Cyclohexanehexone

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Cyclohexanehexone
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Names
IUPAC name
cyclohexane-1,2,3,4,5,6-hexone
Other names
hexaketocyclohexane, triquinoyl
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.649 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9 Yes check.svgY
    Key: PKRGYJHUXHCUCN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9
    Key: PKRGYJHUXHCUCN-UHFFFAOYAM
  • O=C1C(=O)C(=O)C(=O)C(=O)C1=O
Properties
C6O6
Molar mass 168.060 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Cyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is an organic compound with formula C6O6, the sixfold ketone of cyclohexane. It is an oxide of carbon (an oxocarbon), a hexamer of carbon monoxide.

Contents

The compound is expected to be highly unstable, even less stable than the cyclohexanehexathione analog, and as of 1999 had only been observed as an ionized fragment during mass spectrometry studies. [1] [2]

Cyclohexanehexone can be viewed as the neutral counterpart of the rhodizonate anion C6O2−6. The singly charged anion C6O6 has been detected in mass spectrometry experiments, formed by oligomerization of carbon monoxide through the formation of molybdenum carbonyls. [3]

According to X-ray diffraction analysis, the reagent traded under the name "cyclohexanehexone octahydrate" or equivalent names is actually dodecahydroxycyclohexane dihydrate—the geminal 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 formulas C10O8 and C14O10, which can be described as the fusion of two or three molecules of C6O6, claimed to be produced by the action of ultraviolet radiation on a hot water solution of the parent compound. [6]

Triquinoyl therapy

In the late 1940s, William J. Hale claimed that "triquinoyl", being a trimer of William Frederick Koch's glyoxylide, 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 some alternative medicine remedies. [9]

See also

Related Research Articles

<span class="mw-page-title-main">Carbon monoxide</span> Colourless, odourless, tasteless and toxic gas

Carbon monoxide is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simplest carbon oxide. In coordination complexes, the carbon monoxide ligand is called carbonyl. It is a key ingredient in many processes in industrial chemistry.

Carbon compounds are defined as chemical substances containing carbon. More compounds of carbon exist than any other chemical element except for hydrogen. Organic carbon compounds are far more numerous than inorganic carbon compounds. In general bonds of carbon with other elements are covalent bonds. Carbon is tetravalent but carbon free radicals and carbenes occur as short-lived intermediates. Ions of carbon are carbocations and carbanions are also short-lived. An important carbon property is catenation as the ability to form long carbon chains and rings.

<span class="mw-page-title-main">Oxide</span> Chemical compound where oxygen atoms are combined with atoms of other elements

An oxide is a chemical compound containing at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– ion with oxygen in the oxidation state of −2. Most of the Earth's crust consists of oxides. Even materials considered pure elements often develop an oxide coating. For example, aluminium foil develops a thin skin of Al2O3 that protects the foil from further oxidation.

<span class="mw-page-title-main">Acyl group</span> Chemical group (R–C=O)

In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group or hydrogen in the case of formyl group. In organic chemistry, the acyl group is usually derived from a carboxylic acid, in which case it has the formula R−C(=O)−, where R represents an organyl group or hydrogen. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond.

<span class="mw-page-title-main">Radical anion</span> Free radical species

In organic chemistry, a radical anion is a free radical species that carries a negative charge. Radical anions are encountered in organic chemistry as reduced derivatives of polycyclic aromatic compounds, e.g. sodium naphthenide. An example of a non-carbon radical anion is the superoxide anion, formed by transfer of one electron to an oxygen molecule. Radical anions are typically indicated by .

<span class="mw-page-title-main">Molybdenum hexacarbonyl</span> Chemical compound

Molybdenum hexacarbonyl (also called molybdenum carbonyl) is the chemical compound with the formula Mo(CO)6. This colorless solid, like its chromium, tungsten, and seaborgium analogues, is noteworthy as a volatile, air-stable derivative of a metal in its zero oxidation state.

Squaric acid, also called quadratic acid because its four carbon atoms approximately form a square, is a diprotic organic acid with the chemical formula C4O2(OH)2.

<span class="mw-page-title-main">Oxocarbon</span> Chemical compounds made of only carbon and oxygen

In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide. Many other stable or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide and mellitic anhydride.

<span class="mw-page-title-main">Cyclopentanepentone</span> Chemical compound

Cyclopentanepentone, also known as leuconic acid, is a hypothetical organic compound with formula C5O5, the fivefold ketone of cyclopentane. It would be an oxide of carbon (an oxocarbon), indeed a pentamer of carbon monoxide.

<span class="mw-page-title-main">Dodecahydroxycyclohexane</span> Chemical compound

Dodecahydroxycyclohexane is an organic compound with molecular formula C6O12H12 or C6(OH)12 or (C 2)6. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone.

<span class="mw-page-title-main">Ethylene dione</span> Chemical compound

Ethylene dione or ethylenedione, also called dicarbon dioxide, Carbon peroxide, ethenedione, or ethene-1,2-dione, is a chemical compound with the formula C2O2 or O=C=C=O. It is an oxide of carbon, and can be described as the carbon-carbon covalent dimer of carbon monoxide. It can also be thought of as the dehydrated form of glyoxylic acid, or a ketone of ethenone H2C=C=O.

<span class="mw-page-title-main">Benzenehexol</span> Chemical compound

Benzenehexol, also called hexahydroxybenzene, is an organic compound with formula C
6
H
6
O
6
or C
6
(OH)
6
. It is a six-fold phenol of benzene. The product is also called hexaphenol, but this name has been used also for other substances.

<span class="mw-page-title-main">Cyclobutanetetrone</span> Chemical compound

Cyclobutanetetrone, also called tetraoxocyclobutane, is an organic compound with formula C4O4 or (CO)4, the fourfold ketone of cyclobutane. It would be an oxide of carbon, indeed a tetramer of carbon monoxide.

<span class="mw-page-title-main">Croconic acid</span> Chemical compound

Croconic acid is a chemical compound with formula C5H2O5 or (C=O)3(COH)2. It has a cyclopentene backbone with two hydroxyl groups adjacent to the double bond and three ketone groups on the remaining carbon atoms. It is sensitive to light, soluble in water and ethanol and forms yellow crystals that decompose at 212 °C.

<span class="mw-page-title-main">Rhodizonic acid</span> Chemical compound

Rhodizonic acid is a chemical compound with formula H2C6O6 or (CO)4(COH)2. It can be seen as a twofold enol and fourfold ketone of cyclohexene, more precisely 5,6-dihydroxycyclohex-5-ene-1,2,3,4-tetrone.

<span class="mw-page-title-main">Oxocarbon anion</span> Negatively-charged molecule made of carbon and oxygen

In chemistry, an oxocarbon anion is a negative ion consisting solely of carbon and oxygen atoms, and therefore having the general formula C
x
On
y
for some integers x, y, and n.

<span class="mw-page-title-main">Magnesium oxalate</span> Magnesium compound

Magnesium oxalate is an organic compound comprising a magnesium cation with a 2+ charge bonded to an oxalate anion. It has the chemical formula MgC2O4. Magnesium oxalate is a white solid that comes in two forms: an anhydrous form and a dihydrate form where two water molecules are complexed with the structure. Both forms are practically insoluble in water and are insoluble in organic solutions.

<span class="mw-page-title-main">Cyclopropanetrione</span> Chemical compound

Cyclopropanetrione or trioxocyclopropane is a little-known oxide of carbon with formula C3O3. It consists of a ring of three carbon atoms each attached to an oxygen atom with a double bond. Alternately, it can be thought as a trimer of carbon monoxide. This compound is thermodynamically unstable and has not been produced in bulk. However, it has been detected using mass spectrometry.

<span class="mw-page-title-main">Tricarbon monoxide</span> Chemical compound

Tricarbon monoxide C3O is a reactive radical oxocarbon molecule found in space, and which can be made as a transient substance in the laboratory. It can be trapped in an inert gas matrix or made as a short lived gas. C3O can be classified as a ketene or an oxocumulene a kind of heterocumulene.

<span class="mw-page-title-main">Cyclohexanehexathione</span> Chemical compound


Cyclohexanehexathione is a cyclic covalent compound consisting of a six-carbon ring with a sulfur bonded to each. It has been generated by neutralization of its monoanion in a mass spectrometer. This compound is the thioketone analog of cyclohexanehexone; that oxygen variant is expected to be substantially less stable. Synthesis of C6S6 by photolysis or pyrolysis to extrude three equivalents of carbon monoxide from a precursor containing adjacent pairs of sulfurs as cyclic dithiocarbonate units gave what is more likely a different valence isomer, as various dithiete-containing structures are predicted to be more stable than the hexathione form.

References

  1. Gunther Seitz; Peter Imming (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews. 92 (6): 1227–1260. doi:10.1021/cr00014a004.
  2. Schröder, Detlef; Schwarz, Helmut; Dua, Suresh; Blanksby, Stephen J.; Bowie, John H. (1999). "Mass spectrometric studies of the oxocarbons CnOn (n = 3–6)". International Journal of Mass Spectrometry. 188 (1–2): 17–25. Bibcode:1999IJMSp.188...17S. doi:10.1016/S1387-3806(98)14208-2. ISSN   1387-3806.
  3. Wyrwas, Richard B.; Jarrold, Caroline Chick (2006). "Production of C6O6 from Oligomerization of CO on Molybdenum Anions". Journal of the American Chemical Society. 128 (42): 13688–13689. doi:10.1021/ja0643927. PMID   17044687.
  4. Klapötke, Thoman M.; Polborn, Kurt; Weigand, Jan J. (2005). "Dodecahydroxycyclohexane dihydrate". Acta Crystallographica E. 61 (5): o1393–o1395. Bibcode:2005AcCrE..61O1393K. doi:10.1107/S1600536805010007.
  5. Person, Willis B.; Williams, Dale G. (1957). "Infrared Spectra and the Structure of Leuconic Acid and Triquinoyl". The Journal of Physical Chemistry. 61 (7): 1017–1018. doi:10.1021/j150553a047. ISSN   0022-3654.
  6. US 3227641,Worne, Howard E.,"Polycarbonyls",issued 1996-01-04, assigned to Natick Chemical Industries
  7. Hale, William J. (1949). "Farmer Victorious—Money, Mart, and Mother Earth" (reprint).[ permanent dead link ]
  8. 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.
  9. "Import Alert #66-46 – Unapproved Version of Rodaquin". U. S. Food and Drug Administration. 1989. Archived from the original on 2016-11-16. Retrieved 2019-03-09.