The Determination of Ionic Bonding Interactions of N-Phenyl Glycine and N-(2-hydroxy-3-methacryloxypropyl)-N-Phenyl Glycine as Measured by Carbon-13 NMR Analysis

Abstract

The purpose of the present investigation was to determine whether high-resolution carbon-13 nuclear magnetic resonance could be utilized for detection of ionic bonding interactions of NPG and NPG-GMA with selected inorganic cations. The C1-carbonyl carbon of NPG and NPG-GMA were labeled with 13C to help magnify the spectral response signal. The labeled monomers were allowed to react with Ca(OH)2 and LiOH. The C-13 carbonyl resonance was observed by solution- and solid-state NMR. The interaction of the cations in solution and on a powdered glass support resulted in a downfield chemical shift of about 2-5 ppm, indicating the presence of a chemical interaction between the monomer and the cations. The reaction of the monomers with the solid substrates of hydroxyapatite, and bovine dentin did not result in a significant downfield shift in the carbonyl resonance. The results provide evidence that high-resolution nuclear magnetic resonance can be used for evaluation of chemical bonding interactions of dental adhesives with inorganic ions.