1,3,5-Trioxanetrione

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1,3,5-Trioxanetrione
1,3,5-trioxanetrione-2D.png
Chemfm 1 3 5 trioxanetrione.svg
Names
Preferred IUPAC name
1,3,5-Trioxanetrione
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C3O6/c4-1-7-2(5)9-3(6)8-1
    Key: FFPDLONZSMFWAT-UHFFFAOYSA-N
  • O=C1OC(=O)OC(=O)O1
Properties
C3O6
Molar mass 132.027 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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The chemical compound 1,3,5-trioxanetrione, or 1,3,5-trioxacyclohexane-2,4,6-trione is an unstable oxide of carbon with formula C3O6. It can be considered a cyclic trimer of carbon dioxide (CO2) or as a triple ketone of 1,3,5-trioxane (1,3,5-trioxacyclohexane). Trioxanetrione has been synthesized but is exceedingly unstable, with a half-life of approximately 40 min at −40 °C. [1] It decomposes to give carbon dioxide.

Related Research Articles

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.

Trioxane refers to any of three isomeric organic compounds composed of a six-membered ring with three carbon atoms and three oxygen atoms, having the molecular formula C3H6O3.

In chemistry, a trimer is a molecule or polyatomic anion formed by combination or association of three molecules or ions of the same substance. In technical jargon, a trimer is a kind of oligomer derived from three identical precursors often in competition with polymerization.

<span class="mw-page-title-main">1,3,5-Trioxane</span> Chemical compound

1,3,5-Trioxane, sometimes also called trioxane or trioxin, is a chemical compound with molecular formula C3H6O3. It is a white, highly water-soluble solid with a chloroform-like odor. It is a stable cyclic trimer of formaldehyde, and one of the three trioxane isomers; its molecular backbone consists of a six-membered ring with three carbon atoms alternating with three oxygen atoms.

<span class="mw-page-title-main">1,2,4-Trioxane</span> Chemical compound

1,2,4-Trioxane is one of the isomers of trioxane. It has the molecular formula C3H6O3 and consists of a six membered ring with three carbon atoms and three oxygen atoms. The two adjacent oxygen atoms form a peroxide functional group and the other forms an ether functional group. It is like a cyclic acetal but with one of the oxygen atoms in the acetal group being replaced by a peroxide group.

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

In organic chemistry, a carbonate ester is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R−O−C(=O)−O−R' and they are related to esters, ethers and also to the inorganic carbonates.

<span class="mw-page-title-main">Ramberg–Bäcklund reaction</span>

The Ramberg–Bäcklund reaction is an organic reaction converting an α-halo sulfone into an alkene in presence of a base with extrusion of sulfur dioxide. The reaction is named after the two Swedish chemists Ludwig Ramberg and Birger Bäcklund. The carbanion formed by deprotonation gives an unstable episulfone that decomposes with elimination of sulfur dioxide. This elimination step is considered to be a concerted cycloelimination.

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

Carbon trioxide (CO3) is an unstable oxide of carbon (an oxocarbon). The possible isomers of carbon trioxide include ones with molecular symmetry point groups Cs, D3h, and C2v. The C2v state, consisting of a dioxirane, has been shown to be the ground state of the molecule. Carbon trioxide should not be confused with the stable carbonate ion (CO2−
3
).

<span class="mw-page-title-main">1,3,5-Trithiane</span> Chemical compound

1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.

<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">Pentacarbon dioxide</span> Chemical compound

Pentacarbon dioxide, officially penta-1,2,3,4-tetraene-1,5-dione, is an oxide of carbon (an oxocarbon) with formula C5O2 or O=C=C=C=C=C=O.

<span class="mw-page-title-main">1,2-Dioxetanedione</span> Chemical compound

The chemical compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula C2O4. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.

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

Tetracarbon dioxide is an oxide of carbon, a chemical compound of carbon and oxygen, with chemical formula C4O2 or O=C=C=C=C=O. It can be regarded as butatriene dione, the double ketone of butatriene — more precisely 1,2,3-butatriene-1,4-dione.

<span class="mw-page-title-main">1,3-Dioxetanedione</span> Chemical compound

The chemical compound 1,3-dioxetanedione, or 1,3-dioxacyclobutane-2,4-dione, also known as dicarbonic anhydride, is a hypothetical oxide of carbon with formula C2O4. It can be considered a cyclic dimer of carbon dioxide (CO2) or as a double ketone of 1,3-dioxetane (1,3-dioxacyclobutane).

<span class="mw-page-title-main">Triatomic molecule</span> Molecules made of three atoms

Triatomic molecules are molecules composed of three atoms, of either the same or different chemical elements. Examples include H2O, CO2 (pictured), HCN, O3 (ozone) and NO2.

Boron monofluoride or fluoroborylene is a chemical compound with formula BF, one atom of boron and one of fluorine. It was discovered as an unstable gas and only in 2009 found to be a stable ligand combining with transition metals, in the same way as carbon monoxide. It is a subhalide, containing fewer than the normal number of fluorine atoms, compared with boron trifluoride. It can also be called a borylene, as it contains boron with two unshared electrons. BF is isoelectronic with carbon monoxide and dinitrogen; each molecule has 14 electrons.

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

Thioacetone is an organosulfur compound belonging to the -thione group called thioketones, with a chemical formula (CH3)2CS. It is an unstable orange or brown substance that can be isolated only at low temperatures. Above −20 °C (−4 °F), thioacetone readily converts to a polymer and a trimer, trithioacetone. It has an extremely potent, unpleasant odor, and is considered one of the worst-smelling chemicals known to man.

<span class="mw-page-title-main">2,3,4-Pentanetrione</span> Chemical compound

2,3,4-Pentanetrione (or IUPAC name pentane-2,3,4-trione, triketopentane or dimethyl triketone) is the simplest linear triketone, a ketone with three C=O groups. It is an organic molecule with formula CH3COCOCOCH3.

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

Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an organic chemical with formula C
9
H
18
S
3
. Its covalent structure is [–C(CH
3
)
2
–S–]
3
, that is, a six-membered ring of alternating carbon and sulfur atoms, with two methyl groups attached to each carbon. It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group substituents for all of the hydrogen atoms in that parent structure.

References

  1. Rodig, Michael J.; Snow, Arthur W.; Scholl, Paul; Rea, Simon (12 June 2016). "Synthesis and Low Temperature Spectroscopic Observation of 1,3,5-Trioxane-2,4,6-Trione: The Cyclic Trimer of Carbon Dioxide". The Journal of Organic Chemistry. 81 (13): 5354–5361. doi: 10.1021/acs.joc.6b00647 . PMID   27183100. Open Access logo PLoS transparent.svg