Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide

David R. Armstrong; Jonathan Clayden; Robert Haigh; David J. Linton; Paul Schooler; Andrew E H Wheatley

doi:10.1039/b302283h

Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide

David R. Armstrong, Jonathan Clayden, Robert Haigh, David J. Linton, Paul Schooler, Andrew E H Wheatley

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

Abstract

Reaction of 2-ethyl-N,N-diisopropyl-1-naphthamide 3 with ButLi in tetrahydrofuran (thf) affords a laterally metallated derivative which exists as a tris(thf) solvated monomer with no Li-C interaction and an sp2 hybridised carbanionic centre in the solid-state; NMR spectroscopy suggests that this structure is viable in solution but that Li-C bonded atropisomers are also possible and calculations corroborate these data.

Original language	English
Pages (from-to)	1694-1695
Number of pages	1
Journal	Chemical Communications
Volume	9
Issue number	14
DOIs	https://doi.org/10.1039/b302283h
Publication status	Published - 21 Jul 2003

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10.1039/b302283h

CCDC 205221: Experimental Crystal Structure Determination
Armstrong, D. R. (Contributor), Clayden, J. (Contributor), Haigh, R. (Contributor), Linton, D. J. (Contributor), Schooler, P. (Contributor) & Wheatley, A. E. H. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2004
DOI: 10.5517/cc6wk1n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc6wk1n&sid=DataCite
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Cite this

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abstract = "Reaction of 2-ethyl-N,N-diisopropyl-1-naphthamide 3 with ButLi in tetrahydrofuran (thf) affords a laterally metallated derivative which exists as a tris(thf) solvated monomer with no Li-C interaction and an sp2 hybridised carbanionic centre in the solid-state; NMR spectroscopy suggests that this structure is viable in solution but that Li-C bonded atropisomers are also possible and calculations corroborate these data.",

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T1 - Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide

AU - Armstrong, David R.

AU - Clayden, Jonathan

AU - Haigh, Robert

AU - Linton, David J.

AU - Schooler, Paul

AU - Wheatley, Andrew E H

PY - 2003/7/21

Y1 - 2003/7/21

N2 - Reaction of 2-ethyl-N,N-diisopropyl-1-naphthamide 3 with ButLi in tetrahydrofuran (thf) affords a laterally metallated derivative which exists as a tris(thf) solvated monomer with no Li-C interaction and an sp2 hybridised carbanionic centre in the solid-state; NMR spectroscopy suggests that this structure is viable in solution but that Li-C bonded atropisomers are also possible and calculations corroborate these data.

AB - Reaction of 2-ethyl-N,N-diisopropyl-1-naphthamide 3 with ButLi in tetrahydrofuran (thf) affords a laterally metallated derivative which exists as a tris(thf) solvated monomer with no Li-C interaction and an sp2 hybridised carbanionic centre in the solid-state; NMR spectroscopy suggests that this structure is viable in solution but that Li-C bonded atropisomers are also possible and calculations corroborate these data.

U2 - 10.1039/b302283h

DO - 10.1039/b302283h

M3 - Article

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SP - 1694

EP - 1695

JO - Chemical Communications

JF - Chemical Communications

IS - 14

ER -

Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide

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CCDC 205221: Experimental Crystal Structure Determination

Cite this