Oxiranones: α-lactones or zwitterions? Insights from calculated electron density distribution analysis

Giuseppe D. Ruggiero, Ian H. Williams

Research output: Contribution to journalArticle

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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, cyclopropanone, and oxirane. Oxiranone possesses a ring critical point in vacuo, and may be considered as an α-lactone with considerable ionic character in the endocyclic Cα-On bond. In water, oxiranone has neither a ring critical point nor a bond critical point for Cα-On, 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 CαCOn angle of only 69°. Electronically, hydroxyoxiranone is acyclic and zwitterionic even in vacuo, but geometrically it still looks like an α-lactone.

Original languageEnglish
Pages (from-to)733-737
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number5
Early online date5 Apr 2001
Publication statusPublished - 1 Dec 2001

ASJC Scopus subject areas

  • Chemistry(all)

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