Oxiranones: alpha-lactones or zwitterions? Insights from calculated electron density distribution analysis
Ruggiero, G. D. and Williams, I. H., 2001. Oxiranones: alpha-lactones or zwitterions? Insights from calculated electron density distribution analysis. Journal of the Chemical Society: Perkin Transactions 2
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Electron density distributions for oxiranone and hydroxyoxiranone have been analysed in vacuo [MP2/6-31+G(d,p)] and in water [SCI-PCM/MP2/6-31+G(d,p)//HF/6-31+G(d,p)] and compared with those for cyclopropane, cyclo-propanone, and oxirane. Oxiranone possesses a ring critical point in vacuo, and may be considered as an alpha -lactone with considerable ionic character in the endocyclic C-alpha-O-n bond. In water, oxiranone has neither a ring critical point nor a bond critical point for C-alpha-O-n, and may be considered as a zwitterion, whose carboxylate group has a net charge of -0.63. Geometrically, however, the molecule still possesses an acute-angled three-membered ring with a CalphaCOn angle of only 69 degrees. Electronically, hydroxyoxiranone is acyclic and zwitterionic even in vacuo, but geometrically it still looks like an alpha -lactone.
|Creators||Ruggiero, G. D.and Williams, I. H.|
|Departments||Faculty of Science > Chemistry|
|Additional Information||ID number: ISI:000168468900009|
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