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Bioinorganic chemistry of aluminum, gallium. and indium complexes of 1-aryl-3-oxy-4-pyridinones

University of British Columbia

A series of 1-aryl-3-hydroxy-2-methyl-4-pyridinones and tris( 1-aryl-3-oxy-2- methyl-4-pyridinonato)aluminum(III), gallium(III), and indium(III) complexes were prepared and characterized. The 3-hydroxy-4-pyridinones prepared have a variety of aryl substituents at the ring nitrogen atom (phenyl, p-tolyl, p-methoxyphenyl, and p nitrophenyl). The compounds were studied using a number of techniques including single crystal X-ray diffraction, variable temperature NMR spectroscopy, n-octanol/water partitioning, and potentiometric equilibrium measurements. The structures of 3-hydroxy-1-carboxymethyl-2-methyl-4-pyridinone (Hcmp), 3- hydroxy-1-(p-methoxyphenyl)-2-methyl-4-pyridinone (Hpap) and tris(3-oxy-2-methyl-1-p-tolyl)-4-pyridinonato)aluminum(III) (Al(ptp)3) and gallium(III) (Ga(ptp)3) complexes were determined by single crystal X-ray diffraction. A zwitterionic structure is formed in Hcmp as the ketone oxygen is protonated by the carboxyl proton. The metal complexes form rigidfac geometries incorporating hydrogen bonding water molecules which bridge the metal chelating ligand oxygen atoms. [more abstract]

Thesis/Dissertation

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2008-12-16

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http://hdl.handle.net/2429/2984

Chemistry

University of British Columbia

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