A new bis(1-naphthylimino)acenaphthene compound and its Pd(II) and Zn(II) complexes: Synthesis, characterization, solid-state structures and density functional theory studies on the syn and anti isomers

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Abstract

A new rigid bidentate ligand, bis(1-naphthylimino)acenaphthene, L1, and its Zn(II) and Pd(II) complexes [ZnCl2(L1)], 1, and [PdCl 2(L1)], 2, were synthesized. L1 was prepared by the "template method", reacting 1-naphthyl amine and acenaphthenequinone in the presence of ZnCl2, giving 1, which was further demetallated. Reaction of 1-naphthyl amine with acenaphthenequinone and PdCl2 afforded dichloride bis(1-naphthyl)acenaphthenequinonediimine palladium, 2. L1, 1, and 2 were obtained as a mixture of syn and anti isomers. Compound 2 was also obtained by the reaction of PdCl2 activated by refluxing it in acetonitrile followed by the addition of L1; by this route also a mixture of syn and anti isomers was obtained, but at a different rate. The solid-state structures of L1 and the anti isomer of compound 2 have been determined by single-crystal X-ray diffraction. All compounds have been characterized by elemental analyses; matrix-assisted laser desorption ionization-time-of-flight-mass spectrometry; IR; UV-vis; 1H, 13C, and 1H-1H correlation spectroscopy; 1H-13C heteronuclear single quantum coherence; 1H-13C heteronuclear single quantum coherence-total correlation spectroscopy; and 1H-1H nuclear Overhauser effect spectrometry NMR spectroscopies when applied. Density functional theory studies showed that both conformers for [PdCl 2(BIAN)] are isoenergetic, and they can both be obtained experimentally. However, we can predict that the isomerization process is not available in a square-planar complex, but it is possible for the free ligand. The molecular geometry is very similar in both isomers, and only different orientations for naphthyl groups can be expected.

Original languageEnglish
Pages (from-to)7734-7744
Number of pages11
JournalInorganic Chemistry
Volume47
Issue number17
DOIs
Publication statusPublished - 1 Sep 2008

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