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

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

21 Citations (Scopus)

Abstract

Reaction of 2-ethyl-N,N-diisopropyl-1-naphthamide 3 with Bu^tLi 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	2
Journal	Chemical Communications
Volume	9
Issue number	14
Early online date	12 Jun 2003
DOIs	https://doi.org/10.1039/B302283H
Publication status	Published - 21 Jul 2003

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Organic & Biological

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

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.",

author = "Armstrong, \{David R.\} and Jonathan Clayden and Robert Haigh and Linton, \{David J.\} and Paul Schooler and Wheatley, \{Andrew E H\}",

year = "2003",

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doi = "10.1039/B302283H",

language = "English",

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TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/0037625410

U2 - 10.1039/B302283H

DO - 10.1039/B302283H

M3 - Article (Academic Journal)

AN - SCOPUS:0037625410

SN - 1359-7345

VL - 9

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

Abstract

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