Dioxane tetraketone: Difference between revisions
Content deleted Content added
Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation ( |
Citation bot (talk | contribs) Alter: title, journal. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Oxocarbons | #UCB_Category 29/41 |
||
| (17 intermediate revisions by 14 users not shown) | |||
| Line 1: | Line 1: | ||
{{Chembox |
{{Chembox |
||
| Verifiedfields = changed |
|||
| verifiedrevid = |
| verifiedrevid = 441639238 |
||
| Name = |
|||
| ImageFile = Dioxane tetraketone.png |
| ImageFile = Dioxane tetraketone.png |
||
| ImageSize = 120px |
| ImageSize = 120px |
||
| ImageFileL1 = File:Dioxane-tetraketone-3D-balls.png |
|||
| ImageFileR1 = Dioxane-tetraketone-3D-spacefill.png |
|||
| ImageAlt1 = Dioxane tetraketone molecule |
|||
| IUPACName = 1,4-Dioxane-2,3,5,6-tetrone |
| IUPACName = 1,4-Dioxane-2,3,5,6-tetrone |
||
| OtherNames = |
| OtherNames = |
||
| SystematicName = |
|||
| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
||
| CASNo_Ref = {{cascite|correct|??}} |
|||
| CASNo = 213967-57-8 |
| CASNo = 213967-57-8 |
||
| PubChem = |
| PubChem = 10534779 |
||
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|||
| ChemSpiderID = 8710170 |
|||
| SMILES = O=C(O1)C(OC(C1=O)=O)=O |
| SMILES = O=C(O1)C(OC(C1=O)=O)=O |
||
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|||
| StdInChI = 1S/C4O6/c5-1-2(6)10-4(8)3(7)9-1 |
|||
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|||
| StdInChIKey = WBHICAWASPYOHL-UHFFFAOYSA-N |
|||
}} |
}} |
||
| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
||
| C |
| C=4 | O=6 |
||
| Appearance = |
| Appearance = |
||
| Density = |
| Density = |
||
| Line 20: | Line 33: | ||
| MainHazards = |
| MainHazards = |
||
| FlashPt = |
| FlashPt = |
||
| |
| AutoignitionPt = }} |
||
| Section4 = |
|||
| Section5 = |
|||
| Section6 = |
|||
}} |
}} |
||
'''Dioxane tetraketone''' (or '''1,4-dioxane-2,3,5,6-tetrone''') is an [[organic compound]] with the formula C<sub>4</sub>O<sub>6</sub>. It is an [[oxide]] of [[carbon]] (an [[oxocarbon]]), which can be viewed as the fourfold [[ketone]] of [[dioxane]]. It can also be viewed as the [[cyclic compound|cyclic]] [[Dimer (chemistry)|dimer]] of [[oxalic anhydride|oxiranedione]] (C<sub>2</sub>O<sub>3</sub>), the hypothetical [[anhydride]] of [[oxalic acid]]. |
'''Dioxane tetraketone''' (or '''1,4-dioxane-2,3,5,6-tetrone''') is an [[organic compound]] with the formula C<sub>4</sub>O<sub>6</sub>. It is an [[oxide]] of [[carbon]] (an [[oxocarbon]]), which can be viewed as the fourfold [[ketone]] of [[dioxane]]. It can also be viewed as the [[cyclic compound|cyclic]] [[Dimer (chemistry)|dimer]] of [[oxalic anhydride|oxiranedione]] (C<sub>2</sub>O<sub>3</sub>), the hypothetical [[anhydride]] of [[oxalic acid]]. |
||
In 1998, Paolo Strazzolini and others synthesized this compound by reacting [[oxalyl chloride]] (COCl)<sub>2</sub> or the [[oxalyl bromide|bromide]] (COBr)<sub>2</sub> with a suspension of [[silver oxalate]] (Ag<sub>2</sub>C<sub>2</sub>O<sub>4</sub>) in [[diethyl ether]] at |
In 1998, Paolo Strazzolini and others synthesized this compound by reacting [[oxalyl chloride]] (COCl)<sub>2</sub> or the [[oxalyl bromide|bromide]] (COBr)<sub>2</sub> with a suspension of [[silver oxalate]] (Ag<sub>2</sub>C<sub>2</sub>O<sub>4</sub>) in [[diethyl ether]] at −15 °C, followed by evaporation of the solvent at low temperature and pressure. The substance is stable when dissolved in ether and [[trichloromethane]] at −30 °C, but decomposes into a 1:1 mixture of [[carbon monoxide]] (CO) and [[carbon dioxide]] (CO<sub>2</sub>) upon heating to 0 °C.<ref>{{ cite journal | title = The reaction between ethanedioyl (oxalyl) dihalides and Ag<sub>2</sub>C<sub>2</sub>O<sub>4</sub>: a route to Staudinger's elusive ethanedioic (oxalic) acid anhydride |author1=Strazzolini, P. |author2=Gambi, A. |author3=Giumanini, A. G. |author4=Vancik, H. | journal = Journal of the Chemical Society, Perkin Transactions 1 | year = 1998 | volume = 1998 | issue = 16 | pages = 2553–2558 | doi = 10.1039/a803430c }}</ref> The stability and conformation of the molecule were also analyzed by theoretical methods.<ref name="theo">{{ cite journal |author1=Gambi, A. |author2=Guimanini, A. G. |author3=Strazzolini, P. | year = 2001 | title = Theoretical investigations on (CO)<sub>n</sub>(CO<sub>2</sub>)<sub>m</sub> cyclic cooligomers | journal =Journal of Molecular Structure: THEOCHEM | volume = 536 | issue = 1 | pages = 9–16 | doi = 10.1016/S0166-1280(00)00601-1 }}</ref> |
||
{{cite journal |
|||
| title = The reaction between ethanedioyl (oxalyl) dihalides and Ag<sub>2</sub>C<sub>2</sub>O<sub>4</sub>: a route to Staudinger’s elusive ethanedioic (oxalic) acid anhydride |
|||
| author = Paolo Strazzolini, Alberto Gambi, Angelo G. Giumanini and Hrvoj Vancik |
|||
| journal = J. Chem. Soc., Perkin Trans. 1 |
|||
| volume = |
|||
| issue = 16 |
|||
| year = 1998 |
|||
| pages = 2553–2558 |
|||
| doi = 10.1039/a803430c |
|||
}}</ref> The stability and conformation of the molecule were also analyzed by theoretical methods.<ref name="theo"> |
|||
Alberto Gambi, Angelo G. Guimanini, and Paolo Strazzolini (2001), ''Theoretical investigations on (CO)<sub>n</sub>(CO<sub>2</sub>)<sub>m</sub> cyclic cooligomers''. |
|||
Journal of Molecular Structure: THEOCHEM, Volume 536, Issue 1, Pages 9–16 {{doi|10.1016/S0166-1280(00)00601-1}} </ref> |
|||
==References== |
==References== |
||
| Line 47: | Line 51: | ||
[[Category:Oxocarbons]] |
[[Category:Oxocarbons]] |
||
[[Category:Dimers]] |
[[Category:Dimers (chemistry)]] |
||
[[Category: |
[[Category:Carboxylic anhydrides]] |
||
[[Category:Conjugated ketones]] |
|||
[[fr:Dioxanetétracétone]] |
|||
[[hu:Dioxán-tetraketon]] |
|||
[[zh:对二氧杂环己烷四酮]] |
|||