Malonic anhydride: Difference between revisions
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| ImageFile = Malonic anhydride.png |
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| ImageName1 = Ball-and-stick model |
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| = Oxetane-2,4-dione |
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| OtherNames = Malonic anhydride |
| OtherNames = Malonic anhydride |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8351595 |
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| StdInChIKey = KKHUSADXXDNRPW-UHFFFAOYSA-N |
| StdInChIKey = KKHUSADXXDNRPW-UHFFFAOYSA-N |
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| UNII = V8PB6RYA8G |
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| PubChem = 10176090 |
| PubChem = 10176090 |
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| SMILES = O=C1OC(=O)C1 |
| SMILES = O=C1OC(=O)C1 |
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|Section2={{Chembox Properties |
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| C=3|H=2|O=3 |
| C=3|H=2|O=3 |
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'''Malonic anhydride''' or '''oxetane-2,4-dione''' is an [[organic compound]] with [[chemical formula]] C<sub>3</sub>H<sub>2</sub>O<sub>3</sub> or CH<sub>2</sub>(CO)<sub>2</sub>O. It can be viewed as the [[anhydride]] of [[malonic acid]], or a double [[ketone]] of [[oxetane]]. |
'''Malonic anhydride''' or '''oxetane-2,4-dione''' is an [[organic compound]] with [[chemical formula]] C<sub>3</sub>H<sub>2</sub>O<sub>3</sub> or CH<sub>2</sub>(CO)<sub>2</sub>O. It can be viewed as the [[anhydride]] of [[malonic acid]], or a double [[ketone]] of [[oxetane]]. |
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Malonic anhydride was first synthesized in 1988 by [[ozonolysis]] of [[diketene]].<ref>Cotton, F. A.; Wilkinson, G. (1988) ''Advanced Inorganic Chemistry'', 5th edn. Wiley</ref><ref>{{cite journal| title = Paradigms and Paradoxes: Aspects of the Energetics of Carboxylic Acids and Their Anhydrides| author= H. Mark Perks and Joel F. Liebman| journal= Structural Chemistry | year = 2000| pages = 265–269| volume = 11| issue = 4 | doi = 10.1023/A:1009270411806| s2cid= 92816468| issn = 1040-0400}}</ref> Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione, are known.<ref>Charles L. Perrin; Arrhenius, T (1978). J. Am. Chem. SOC. volume 100, pages 5249-5251.</ref><ref>Ribeiro da Silva, M. A. J.; Monte, M. J. S.; Ribeiro, J. R.(1999) ''J. Chem.Thermodyn.'' 31, 1093.</ref><ref>Charles L. Perrin, Douglas Magde, Sylvia J. Berens, Julie Roque (1980), ''Raman spectrum of a malonic anhydride''. (Actually, of 3,3-dimethyl-oxetane-2,4-dione.) J. Org. Chem., volume 45 issue 9, pp 1705–1706. {{doi|10.1021/jo01297a044}}.</ref> |
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Malonic anhydride was first synthesized in 1988 by [[ozonolysis]] of [[diketene]].<ref> |
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Cotton, F. A.; Wilkinson, G. (1988) ''Advanced Inorganic Chemistry'', 5th edn. Wiley |
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</ref><ref> |
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{{cite journal |
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| title = Paradigms and Paradoxes: Aspects of the Energetics of Carboxylic Acids and Their Anhydrides |
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| author= H. Mark Perks and Joel F. Liebman |
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| journal= Structural Chemistry |
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| year = 2000 |
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| pages = 265269 |
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| volume = 11 |
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| issue = 4 |
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| doi = 10.1023/A:1009270411806 |
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| issn = 1040-0400 |
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}} |
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</ref> Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione, are known.<ref> |
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Charles L. Perrin; Arrhenius, T (1978). J. Am. Chem. SOC. volume 100, pages 5249-5251. |
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</ref><ref> |
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Ribeiro da Silva, M. A. J.; Monte, M. J. S.; Ribeiro, J. R.(1999) ''J. Chem.Thermodyn.'' 31, 1093. |
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</ref><ref> |
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Charles L. Perrin, Douglas Magde, Sylvia J. Berens, Julie Roque (1980), ''Raman spectrum of a malonic anhydride''. (Actually, of 3,3-dimethyl-oxetane-2,4-dione.) J. Org. Chem., volume 45 issue 9, pp 1705–1706. DOI: 10.1021/jo01297a044. |
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</ref> |
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{{Reflist}} |
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==See also== |
==See also== |
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* [[3-oxetanone]] |
* [[3-oxetanone]] |
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<references /> |
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[[Category:Oxetanes]] |
[[Category:Oxetanes]] |
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[[Category:Substances discovered in the 1980s]] |
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[[fr:Anhydride malonique]] |
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[[hu:Malonsav-anhidrid]] |
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[[pt:Anidrido malônico]] |