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

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

20 Citations (Scopus)

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 languageEnglish
Pages (from-to)1694-1695
Number of pages2
JournalChemical Communications
Volume9
Issue number14
Early online date12 Jun 2003
DOIs
Publication statusPublished - 21 Jul 2003

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