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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Published Version
Date
2015-09-08
Authors
Bateman, Lorraine M.
McNamara, Orla A.
Buckley, N. Rachael
O'Leary, Patrick
Harrington, Francis
Kelly, Norma
O'Keeffe, Sarah
Stack, Angela
O'Neill, Shane T.
McCarthy, Daniel G.
Journal Title
Journal ISSN
Volume Title
Publisher
The Royal Society of Chemistry
Published Version
Abstract
A 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.
Description
Keywords
Positive ions , Cycloheptatrienes , Electronic characteristics , NMR studies , Variable temperature , Nuclear magnetic resonance spectroscopy
Citation
BATEMAN, 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/C5OB01346A