| Revision as of 11:48, 21 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CASNo').← Previous edit |
Latest revision as of 09:55, 17 October 2022 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Cycloalkanones; added Category:Cyclic ketones using HotCat |
| (28 intermediate revisions by 18 users not shown) |
| Line 2: |
Line 2: |
|
| Verifiedfields = changed |
|
| Verifiedfields = changed |
|
| Watchedfields = changed |
|
| Watchedfields = changed |
|
| verifiedrevid = 410048575 |
|
| verifiedrevid = 456664709 |
|
⚫ |
| Name = |
|
| ImageFile = Cyclobutanetetrone.png |
|
| ImageFile = Cyclobutanetetrone.png |
|
|
| ImageFile1 = File:Chemfm cyclobutanetetrone.svg |
|
| ImageFile_Ref = {{chemboximage|correct|??}} |
|
| ImageFile_Ref = {{chemboximage|correct|??}} |
|
|
| ImageSize1 = 121 |
|
| ImageSize = 121 |
|
| ImageSize = 121 |
|
| ImageName = Skeletal formula of cyclobutanetetrone |
|
| ImageName = Skeletal formula of cyclobutanetetrone |
|
| IUPACName = Cyclobutane-1,2,3,4-tetraone{{Citation needed|date = May 2011}} |
|
| IUPACName = Cyclobutane-1,2,3,4-tetraone{{Citation needed|date = May 2011}} |
|
| OtherNames = Tetraoxocyclobutane |
|
| OtherNames = Tetraoxocyclobutane |
|
|
| SystematicName = |
|
| Section1 = {{Chembox Identifiers |
|
| Section1 = {{Chembox Identifiers |
|
| CASNo_Ref = {{cascite|correct|??}} |
|
| CASNo_Ref = {{cascite|changed|??}} |
|
| CASNo = <!-- blanked - oldvalue: 3617-57-0 --> |
|
| CASNo = 76719-54-5 |
|
| ChemSpiderID = 24735246 |
|
| ChemSpiderID = 24735246 |
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| SMILES = O=C1C(=O)C(=O)C1=O |
|
| PubChem = 5488007 |
|
|
| SMILES = O=C1C(=O)C(=O)C1=O |
|
| StdInChI = 1S/C4O4/c5-1-2(6)4(8)3(1)7 |
|
| StdInChI = 1S/C4O4/c5-1-2(6)4(8)3(1)7 |
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = KDAVZOLBYGNLGF-UHFFFAOYSA-N |
|
| StdInChIKey = KDAVZOLBYGNLGF-UHFFFAOYSA-N |
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
| Section2 = {{Chembox Properties |
|
| C = 4 |
|
| C=4 | O=4 |
| ⚫ |
| O = 4 |
|
|
| ExactMass = 111.979658488 g mol<sup>-1</sup> |
|
|
}} |
|
}} |
|
|
| Section3 = |
|
|
| Section4 = |
|
|
| Section5 = |
|
|
| Section6 = |
|
}} |
|
}} |
|
|
|
|
|
'''Cyclobutanetetrone''', also called '''tetraoxocyclobutane''', is a hypothetical ] with formula C<sub>4</sub>O<sub>4</sub> or (-(C=O)-)<sub>4</sub>, the fourfold ] of ]. It would be an ], indeed a ] of ]. |
|
'''Cyclobutanetetrone''', also called '''tetraoxocyclobutane''', is an ]<ref>{{ cite journal |last1=Guo |first1=J.-C. |last2=Hou |first2=G.-L. |last3=Li |first3=S.-D. |last4=Wang |first4=X.-B. | year = 2012 | title = Probing the Low-Lying Electronic States of Cyclobutanetetraone (C<sub>4</sub>O<sub>4</sub>) and Its Radical Anion: A Low-Temperature Anion Photoelectron Spectroscopic Approach| journal = Journal of Physical Chemistry A | volume = 3 | issue = 3 | pages = 304–308 | doi = 10.1021/jz201593z|pmid=26285843 }}</ref> with formula C<sub>4</sub>O<sub>4</sub> or (CO)<sub>4</sub>, the fourfold ] of ]. It would be an ], indeed a ] of ]. |
|
|
|
|
|
|
The compound seems to be thermodynamically unstable.<ref>{{ cite journal |last1=Jiao |first1=H. |last2=Frapper |first2=G. |last3=Halet |first3=J.-F. |last4=Saillard |first4=J.-Y. | year = 2001 | title = Stability of Tetraoxocyclobutane Revised: Perturbation Theory and Density Functional Scheme | journal = Journal of Physical Chemistry Letters | volume = 105 | issue = 24 | pages = 5945–5947 | doi = 10.1021/jp010738i |bibcode=2001JPCA..105.5945J }}</ref> As of 2000, it had yet to be synthesized in significant amounts<ref name="rubin">{{ cite journal |last1=Rubin |first1=M. B. |last2=Gleiter |first2=R. | year = 2000 | title = The Chemistry of Vicinal Polycarbonyl Compounds | journal = Chemical Reviews | volume = 100 | issue = 3 | pages = 1121–1164 | doi = 10.1021/cr960079j | pmid=11749259}}</ref><ref name="seitz">{{ cite journal | title = Oxocarbons and pseudooxocarbons |last1=Seitz |first1=G. |last2=Imming |first2=P. | journal = Chemical Reviews | year = 1992 | volume = 92 | issue = 6 | pages = 1227–1260 | doi = 10.1021/cr00014a004 }}</ref> but may have transient existence as detected by ].<ref>{{ cite journal | title = Mass spectrometric studies of the oxocarbons C<sub>''n''</sub>O<sub>''n''</sub> (''n'' = 3–6) |last1=Schröder |first1=D. |last2=Schwarz |first2=H. |last3=Dua |first3=S. |last4=Blanksby |first4=S. J. |last5=Bowie |first5=J. H. | doi = 10.1016/S1387-3806(98)14208-2 | journal = International Journal of Mass Spectrometry | volume = 188 | issue = 1–2 | year = 1999 | pages = 17–25 |bibcode=1999IJMSp.188...17S }}</ref> |
|
The compound seems to be thermodynamically unstable.<ref> |
|
|
Haijun Jiao, Gilles Frapper, Jean-François Halet, and Jean-Yves Saillard (2001), ''Stability of Tetraoxocyclobutane Revised: Perturbation Theory and Density Functional Scheme''. J. Phys. Chem. A, volume 105 issue 24, pp. 5945–5947. DOI: 10.1021/jp010738i |
|
|
</ref> As of 2000, it had yet to be synthesized in significant amounts<ref name="rubin"> |
|
|
Mordecai B. Rubin and Rolf Gleiter (2000), ''The Chemistry of Vicinal Polycarbonyl Compounds''. Chemical Reviews, volume 100 issue 3, pp. 1121–1164. DOI: 10.1021/cr960079j |
|
|
</ref><ref name="seitz"> |
|
|
{{cite journal |
|
|
| title = Oxocarbons and pseudooxocarbons |
|
|
| author = Gunther Seitz |
|
|
| coauthors = Peter Imming |
|
|
| journal = Chemical Reviews |
|
|
| year = 1992 |
|
|
| volume = 92 |
|
|
| issue = 6 |
|
|
| pages = 1227–1260 |
|
|
| doi = 10.1021/cr00014a004 |
|
|
| url = http://admin.pubs.acs.org/doi/pdf/10.1021/cr00014a004 |
|
|
}}</ref> but may have transient existence as detected by ].<ref> |
|
|
{{cite journal |
|
|
| title = Mass spectrometric studies of the oxocarbons CnOn (n = 3–6) |
|
|
| author = Detlef Schröder, |
|
|
| coauthors = ], Suresh Dua, Stephen J. Blanksby and John H. Bowie |
|
|
| doi = 10.1016/S1387-3806(98)14208-2 |
|
|
| journal = International Journal of Mass Spectrometry |
|
|
| volume = 188 |
|
|
| issue = 1–2 |
|
|
| month = May |
|
|
| year = 1999 |
|
|
| pages = 17–25 |
|
|
}}</ref> |
|
|
|
|
|
|
==Related compounds== |
|
==Related compounds== |
|
|
|
|
|
Cyclobutanetetrone can be viewed as the neutral counterpart of the ] ] C<sub>4</sub>O<sub>4</sub><sup>2−</sup>, which is stable and has been known at least since 1959.<ref>{{cite journal |last1= Cohen |first1= Sidney |last2= Lacher |first2= John R. |last3= Park |first3= Joseph D. |author9= Sidney Cohen, John R. Lacher, Joseph D. Park |year= 1959 |title= Diketocyclobutanediol |journal= J. Am. Chem. Soc. |volume= 81 |pages= 3480 |doi= 10.1021/ja01522a083 |issue= 13 }}</ref> |
|
Cyclobutanetetrone can be viewed as the neutral counterpart of the ] ] {{chem|C|4|O|4|2-}}, which is stable and has been known at least since 1959.<ref>{{ cite journal | last1 = Cohen | first1 = S. | last2 = Lacher | first2 = J. R. | last3 = Park | first3 = J. D. | title = Diketocyclobutanediol | journal = Journal of the American Chemical Society | year = 1959 | volume = 81 | issue = 13 | pages = 3480 | doi = 10.1021/ja01522a083 }}</ref> |
|
|
|
|
|
The compound ] or cyclobutane-1,1,2,2,3,3,4,4-octaol (-C(OH)<sub>2</sub>-)<sub>4</sub> may be referred to in the literature as "hydrated tetraoxocyclobutane".<ref>{{ cite journal |last1= Skujins |first1= S. |last2= Delderfield |first2= J. |last3= Webb |first3= G.A. |author9= S. Skujins, J. Delderfield and G. A. Webb |year= 1967 |title= A mass spectrometric study of some monocyclic polycarbonyl compounds |journal= Tetrahedron |volume= 24 |issue= 13 |pages= 4805–4817 |doi= 10.1016/S0040-4020(01)98676-4 }}</ref> |
|
The compound ] or cyclobutaneoctaol (C(OH)<sub>2</sub>)<sub>4</sub> may be referred to in the literature as "hydrated tetraoxocyclobutane".<ref>{{ cite journal | last1 = Skujins | first1 = S. | last2 = Delderfield | first2 = J. | last3 = Webb | first3 = G. A. | title = A mass spectrometric study of some monocyclic polycarbonyl compounds | journal = Tetrahedron | year = 1967 | volume = 24 | issue = 13 | pages = 4805–4817 | doi = 10.1016/S0040-4020(01)98676-4 }}</ref> |
|
|
|
|
|
==References== |
|
==References== |
|
{{Reflist}} |
|
{{Reflist}} |
|
|
{{refbegin}} |
|
* G. Maahs, P. Hegenberg (2003), ''Syntheses and Derivatives of Squaric Acid''. Angewandte Chemie Int. Ed., Volume 5 Issue 10, Pages 888–893. DOI: 10.1002/anie.196608881 |
|
* {{ cite journal |last1=Maahs |first1=G. |last2=Hegenberg |first2=P. | year = 2003 | title = Syntheses and Derivatives of Squaric Acid | journal = Angewandte Chemie International Edition | volume = 5 | issue = 10 | pages = 888–893 | doi = 10.1002/anie.196608881 }} |
|
|
{{refend}} |
|
|
|
|
|
==See also== |
|
==See also== |
| Line 76: |
Line 57: |
|
] |
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
|
] |
|
] |
|
|
|
] |
|
] |
|