title: Protonation behavior and solution properties of amine oxide surfactants containing a pyridyl group.
abstract: Hydrogen bonding between surfactant molecules plays an important role in self-assembly formation. For long alkyl chain amine oxide surfactants, the specific protonation degree dependence of some solution properties has been considered to be due to hydrogen bonding between protonated and deprotonated species. In addition to this type of hydrogen bonding, we introduced a pyridyl group into an alkylamine oxide molecule as a new hydrogen-bonding site. The pyridyl group has three different structural isomers based on the position of the substituent. An amine oxide group in pyridylamine oxides was preferentially protonated. In addition, protonation of the pyridyl group revealed a pronounced substituent position effect on the critical micelle concentration, micellar size, and solubilization of oil-soluble dye into micelles. The intermolecular or intramolecular hydrogen bond formation could be controlled by altering the substituent position.
authors.affiliation: Organic Materials Research Division, Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka 836-8553, Japan. rie@omtri.or.jp
authors.forename: R
authors.initials: R
authors.lastname: Kakehashi
authors.forename: N
authors.initials: N
authors.lastname: Tokai
authors.forename: T
authors.initials: T
authors.lastname: Kohno
authors.forename: Y
authors.initials: Y
authors.lastname: Nakatsuji
authors.forename: S
authors.initials: S
authors.lastname: Yamamura
authors.forename: G
authors.initials: G
authors.lastname: Karlsson
mesh_terms: D000588:Amines / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D011522:Protons; D011725:Pyridines / Q000737:chemistry*; D012996:Solutions; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D000588:Amines; D010087:Oxides; D011522:Protons; D011725:Pyridines; D012996:Solutions; D013501:Surface-Active Agents