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A homologous series of crown-ether-complexed alkali metal amides as discrete ion-pair species: Synthesis and structures of [M(12-crown-4) 2][PyNPh·PyN(H)Ph] (M = Li, Na and K)

Lookup NU author(s): Dr Stephen Liddle, Emeritus Professor Bill CleggORCiD


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Reaction between one equivalent of n-butyllithium and 2-phenylaminopyridine, in the presence of 12-crown-4 ether (12C4) in toluene, affords the discrete ion-pair complex [{Li(12C4)2} {N(Py)(Ph)·HN(Py)(Ph)}] (1), in which the secondary amine proton is hydrogen-bonded to the secondary amide anion. Compound 1 is the sole isolable product of this reaction, irrespective of the amount of lithium alkyl employed, metallation never exceeding 50%. Metathesis of 1 with sodium- or potassium-tert-butoxide affords the homologous complexes [{Na(12C4) 2} {N(Py)(Ph)·HN(Py)(Ph)}] (2) and [{K(12C4)2} {N(Py)(Ph)·HN(Py)(Ph)}] (3), respectively. Compounds 1, 2 and 3 have all been characterised by X-ray crystallography, NMR spectroscopy and elemental analysis. © 2003 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Liddle ST, Clegg W

Publication type: Article

Publication status: Published

Journal: Polyhedron

Year: 2003

Volume: 22

Issue: 27

Pages: 3507-3513

ISSN (print): 0277-5387

ISSN (electronic): 1873-3719

Publisher: Pergamon


DOI: 10.1016/j.poly.2003.09.011


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