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The conformational and quantum analyses of dental adhesive carboxylic acid and carboxylic acid anhydride monomers were preformed. Conformational analyses were carried out by a molecular mechanics calculation. 4-META and 4-AETA showed more compact conformation than 4-MET. Quantum analyses were performed by semi-empirical molecular orbital calculation. 4-MET had a higher dipole moment, polarizability, and HOMO and LUMO energy than 4-META and 4-AETA. The bond lengths and bond orders of the carbonyl groups of the trimellitic acid moiety of 4-MET were different from those of carbonyl groups of the trimellitate anhydride moieties of 4-META and 4-AETA. Oxygen of the methacryloyl or acryloyl groups showed the highest electron densities among the oxygen atoms for all monomers. The superdelocalizabilities of oxygen atoms of the trimellitic acid moiety of 4-MET were greater than that of oxygen of the methacryloyl group. A small change in the bond length of the Ca-O bond showed a large difference in the steric energies of 4-MET/Ca salt.

Conformational and Quantum Analysis of Dental Adhesive Carboxylic Acid and Carboxylic Acid Anhydride Monomers.