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Journal of Dental Research
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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

L.E. Wolinsky

School of Dentistry, University of California at Los Angeles, Section of Oral Biology, 405 Hilgard Avenue, Los Angeles, CA 90024-1668

R.W. Armstrong

Department of Chemistry, University of California at Los Angeles, Los Angeles, California 90024

R.R. Seghi

College of Dentistry, The Ohio State University, Columbus, Ohio 43210

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.

Journal of Dental Research, Vol. 72, No. 1, 72-77 (1993)
DOI: 10.1177/00220345930720011101
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L.E. Tam and R.M. Pilliar
Fracture Surface Characterization of Dentin-bonded Interfacial Fracture Toughness Specimens
Journal of Dental Research, March 1, 1994; 73(3): 607 - 619.
[Abstract] [PDF]