Infrared and Photoacoustic Spectroscopic Studies of a Silica-Immobilized β-Diketone

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Abstract
Infrared and photoacoustic spectroscopies have in combination produced useful information about an immobilized β-diketone, formed by the reaction of acetylacetone with p-chloromethylphenyltrimethoxysilane previously immobilized on silica. Evidence confirming the synthesis of immobilized 3-benzyl-2,4-pentanedione is presented. Comparisons with 3-benzyl-2,4-pentanedione, a model for the surface bonded ligand, were valuable. The bound β-diketone is largely in the keto tautomer on the surface. The photoacoustic spectrum shows that the remainder is in the form of an intermolecular hydrogen-bonded enol. In basic solution the enolate ion and metal-enolate complexes can be formed. Infrared spectra show that the keto form can bind metals in acidic solutions.