title: Conformational and quantum analysis of dental adhesive carboxylic acid and carboxylic acid anhydride monomers.
abstract: 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.
authors.affiliation: Department of Dental Materials, Nihon University School of Dentistry at Matsudo, 2-870-1 Sakaecho Nishi, Matsudo, Chiba, 271-8587, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Hayakawa
authors.forename: K
authors.initials: K
authors.lastname: Kikutake
authors.forename: K
authors.initials: K
authors.lastname: Nemoto
mesh_terms: D000269:Adhesives / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D001840:Dental Bonding; D003738:Dental Cements / Q000737:chemistry*; D008422:Materials Testing; D008689:Methacrylates / Q000737:chemistry*; D008968:Molecular Conformation; D011789:Quantum Theory; D014233:Tricarboxylic Acids / Q000737:chemistry
chemical_list: D000269:Adhesives; D002264:Carboxylic Acids; D003738:Dental Cements; D008689:Methacrylates; D014233:Tricarboxylic Acids; C034139:4-methacryloxyethyltrimellitic acid anhydride; C014871:trimellitic acid