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 a Journal (Peer & Non Peer) › Article › peer-review

22 Citations (Scopus)

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
Externally published	Yes

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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

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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 a Journal (Peer & Non Peer) › 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

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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