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

Lorraine M. Bateman; Orla A. McNamara; N. Rachael Buckley; Patrick O'Leary; Francis Harrington; Norma Kelly; Sarah O'Keeffe; Angela Stack; Shane O'Neill; Daniel G. McCarthy; Anita R. Maguire

doi:10.1039/c5ob01346a

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

Lorraine M. Bateman
, Orla A. McNamara
, N. Rachael Buckley
, Patrick O'Leary
, Francis Harrington
, Norma Kelly
, Sarah O'Keeffe
, Angela Stack
, Shane O'Neill
, Daniel G. McCarthy
, Anita R. Maguire

University College Cork

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	11026-11038
Number of pages	13
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	45
DOIs	https://doi.org/10.1039/c5ob01346a
Publication status	Published - 8 Sep 2015

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10.1039/c5ob01346a

https://hdl.handle.net/10468/2177Licence: CC BY

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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 and Biomolecular Chemistry, 13(45), 11026-11038. https://doi.org/10.1039/c5ob01346a

@article{719bc3a51c0e45588c63ca78adac4737,

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

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.",

author = "Bateman, \{Lorraine M.\} and McNamara, \{Orla A.\} and Buckley, \{N. Rachael\} and Patrick O'Leary and Francis Harrington and Norma Kelly and Sarah O'Keeffe and Angela Stack and Shane O'Neill and McCarthy, \{Daniel G.\} and Maguire, \{Anita R.\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2015",

month = sep,

day = "8",

doi = "10.1039/c5ob01346a",

language = "English",

volume = "13",

pages = "11026--11038",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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}

Bateman, LM, McNamara, OA, Buckley, NR, O'Leary, P, Harrington, F, Kelly, N, O'Keeffe, S, Stack, A, O'Neill, S, McCarthy, DG & Maguire, AR 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 and Biomolecular Chemistry, vol. 13, no. 45, pp. 11026-11038. https://doi.org/10.1039/c5ob01346a

A study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium. / Bateman, Lorraine M.; McNamara, Orla A.; Buckley, N. Rachael et al.
In: Organic and Biomolecular Chemistry, Vol. 13, No. 45, 08.09.2015, p. 11026-11038.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - A study of the norcaradiene-cycloheptatriene equilibrium in a series of azulenones by NMR spectroscopy; the impact of substitution on the position of equilibrium

AU - Bateman, Lorraine M.

AU - McNamara, Orla A.

AU - Buckley, N. Rachael

AU - O'Leary, Patrick

AU - Harrington, Francis

AU - Kelly, Norma

AU - O'Keeffe, Sarah

AU - Stack, Angela

AU - O'Neill, Shane

AU - McCarthy, Daniel G.

AU - Maguire, Anita R.

PY - 2015/9/8

Y1 - 2015/9/8

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84947297211

U2 - 10.1039/c5ob01346a

DO - 10.1039/c5ob01346a

M3 - Article

AN - SCOPUS:84947297211

SN - 1477-0520

VL - 13

SP - 11026

EP - 11038

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 45

ER -

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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