A study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium

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dc.contributor.authorBateman, Lorraine M.
dc.contributor.authorMcNamara, Orla A.
dc.contributor.authorBuckley, N. Rachael
dc.contributor.authorO'Leary, Patrick
dc.contributor.authorHarrington, Francis
dc.contributor.authorKelly, Norma
dc.contributor.authorO'Keeffe, Sarah
dc.contributor.authorStack, Angela
dc.contributor.authorO'Neill, Shane T.
dc.contributor.authorMcCarthy, Daniel G.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderEnterprise Irelanden
dc.contributor.funderHigher Education Authorityen
dc.contributor.funderIrish Research Council for Science Engineering and Technologyen
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderPfizer Pharmaceuticalsen
dc.contributor.funderUniversity College Corken
dc.contributor.funderCork Corporationen
dc.contributor.funderCork County Councilen
dc.contributor.funderRoyal Irish Academyen
dc.date.accessioned2016-01-12T11:04:12Z
dc.date.available2016-01-12T11:04:12Z
dc.date.issued2015-09-08
dc.description.abstractA systematic investigation of the influence of substitution at positions C-2 and C-3 on the azulenone skeleton, based on NMR characterisation, is discussed with particular focus on the impact of the steric and electronic characteristics of substituents on the position of the norcaradiene-cycloheptatriene (NCD-CHT) equilibrium. Variable temperature (VT) NMR studies, undertaken to enable the resolution of signals for the equilibrating valence tautomers revealed, in addition, interesting shifts in the equilibrium.en
dc.description.sponsorshipHigher Education Authority (PRTLI3 Studentships); Irish Research Council for Science Engineering and Technology (Studentships); Science Foundation Ireland (SFI Advance Award (14/ADV/RC2751)); Pfizer Pharmaceuticals (Studentships); University College Cork (UCC President's Research Fund)en
dc.description.statusPeer revieweden
dc.description.versionPublished Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationBATEMAN, L. M., MCNAMARA, O. A., BUCKLEY, N. R., O'LEARY, P., HARRINGTON, F., KELLY, N., O'KEEFFE, S., STACK, A., O'NEILL, S., MCCARTHY, D. G. & MAGUIRE, A. R. 2015. A study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium. Organic & Biomolecular Chemistry, 13, 11026-11038. http://dx.doi.org/10.1039/C5OB01346Aen
dc.identifier.doi10.1039/C5OB01346A
dc.identifier.endpage11038en
dc.identifier.issn1477-0520
dc.identifier.issued45en
dc.identifier.journaltitleOrganic & Biomolecular Chemistryen
dc.identifier.startpage11026en
dc.identifier.urihttps://hdl.handle.net/10468/2177
dc.identifier.volume13en
dc.language.isoenen
dc.publisherThe Royal Society of Chemistryen
dc.rights© 2015, the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.en
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/en
dc.subjectPositive ionsen
dc.subjectCycloheptatrienesen
dc.subjectElectronic characteristicsen
dc.subjectNMR studiesen
dc.subjectVariable temperatureen
dc.subjectNuclear magnetic resonance spectroscopyen
dc.titleA study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibriumen
dc.typeArticle (peer-reviewed)en
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