Three-membered ring amides — a calculational and conceptual study of the structure and energetics of 1,2-oxaziridine-3-one and aziridine-2,3-dione

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dc.contributor.authorMiranda, Margarida S.
dc.contributor.authorFerreira, Paulo J.O.
dc.contributor.authorSilva, Joaquim C.G. Esteves da
dc.contributor.authorLiebman, Joel F.
dc.date.accessioned2018-10-01T14:05:12Z
dc.date.available2018-10-01T14:05:12Z
dc.date.issued2104-07-28
dc.description.abstractSpecies with three-membered rings and the amide linkage are well studied. A quick perusal of the literature with SciFinder finds some 50 000 references to cyclopropanes and almost 300 000 references to amides. In the current paper, we discuss the structure and energetics of two understudied three-membered ring amides, 1,2-oxaziridine-3-one (5) (simultaneously describable as the simplest cyclic carbamate and simplest hydroxamate) and aziridine-2,3-dione (7) (simultaneously describable as the simplest imide and simplest -ketoamide), with but 5 and nearly 10 references, respectively, for these two classes of compounds. Neither 1,2-oxaziridine-3-one (5) nor aziridine-2,3-dione (7), nor any derivative thereof, has been isolated. Calculational theory ameliorates the paucity of experimental information. The current study reports our computational findings for these and related species (e.g., enols and imidols) where we have used the G3(MP2)//B3LYP method.en_US
dc.description.sponsorshipM. S. Miranda thanks the Fundação para a Ciência e a Tecnologia (FCT; Lisbon, Portugal) for the financial support under the Ciência 2008 program.en_US
dc.description.urihttp://www.nrcresearchpress.com/doi/full/10.1139/cjc-2014-0321#.W606G3tKiAZen_US
dc.format.extent8 pagesen_US
dc.genrejournal articleen_US
dc.identifierdoi:10.13016/M2JW86R4W
dc.identifier.citationMargarida S. Miranda, Paulo J.O. Ferreira, Joaquim C.G. Esteves da Silva, Joel F. Liebman » Abstract Canadian Journal of Chemistry, 2015, 93:406-413, https://doi.org/10.1139/cjc-2014-0321en_US
dc.identifier.urihttps://doi.org/10.1139/cjc-2014-0321
dc.identifier.urihttp://hdl.handle.net/11603/11422
dc.language.isoen_USen_US
dc.publisherCanadian Scienceen_US
dc.relation.isAvailableAtThe University of Maryland, Baltimore County (UMBC)
dc.relation.ispartofUMBC Chemistry & Biochemistry Department Collection
dc.relation.ispartofUMBC Faculty Collection
dc.rightsThis item is likely protected under Title 17 of the U.S. Copyright Law. Unless on a Creative Commons license, for uses protected by Copyright Law, contact the copyright holder or the author.
dc.subjectamidesen_US
dc.subjectcyclopropane and cyclopropanone derivativesen_US
dc.subjectenthalpy of formationen_US
dc.subjectmolecular structure and energeticsen_US
dc.subjectstrained organic moleculesen_US
dc.subjectUMBC High Performance Computing Facility (HPCF)en_US
dc.titleThree-membered ring amides — a calculational and conceptual study of the structure and energetics of 1,2-oxaziridine-3-one and aziridine-2,3-dioneen_US
dc.typeTexten_US

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