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American Chemical Society, Inorganic Chemistry, 26(41), p. 6956-6958, 2002

DOI: 10.1021/ic026004h

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Intramolecular “Aryl−Metal Chelate Ring” π,π-Interactions as Structural Evidence for Metalloaromaticity in (Aromatic α,α‘-Diimine)−Copper(II) Chelates: Molecular and Crystal Structure of Aqua(1,10-phenanthroline)(2-benzylmalonato)copper(II) Three-hydrate

Journal article published in 2002 by A. Castiñeiras, A. G. Sicilia Zafra, J. M. González Pérez ORCID, D. Choquesillo Lazarte ORCID, J. Niclós Gutiérrez
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

By reaction of Cu(2)CO(3)(OH)(2), 2-benzylmalonic acid (H(2)Bzmal), and 1,10-phenanthroline (phen), [Cu(Bzmal)(phen)(H(2)O)] x 3H(2)O (compound 1) has been obtained and characterized by thermal, spectral, magnetic, and X-ray diffraction methods. The molecular structure of 1 is remarkably similar to that of [Cu(Bzmal)(bipy)(H(2)O)] x 2H(2)O (compound 2, bipy = 2,2'-bipyridine). In both complexes, the aryl(Bzmal) ring produces an unexpected pi,pi-stacking interaction with the Cu(II)-(aromatic alpha,alpha'-diimine) chelate ring, at an average distance d(pi)(-)(pi) of 3.40 A, involving roughly parallel and smoothly slipped rings. This insight is discussed as new structural evidence for metalloaromaticity of Cu(II)-(aromatic alpha,alpha'-diimine) chelate rings. Interestingly, 1 recognizes itself by a weak intermolecular pi,pi-stacking interaction between aryl(Bzmal) ligands to give pairs of complex molecules. In contrast, there is an intermolecular pyridyl-pyridyl pi,pi-stacking interaction also forming pairs of complex molecules in 2.