Protonation Behavior and Solution Properties of Amine Oxide Surfactants Containing a Pyridyl Group

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...

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Bibliographic Details
Published inJournal of Oleo Science Vol. 62; no. 3; pp. 123 - 132
Main Authors Kakehashi, R., Tokai, N., Kohno, T., Nakatsuji, Y., Yamamura, S., Karlsson, G.
Format Journal Article
LanguageEnglish
Published Japan Japan Oil Chemists' Society 2013
Japan Science and Technology Agency
Subjects
Amines - chemistry
hydrogen bond
Hydrogen Bonding
Molecular Structure
Oxides - chemistry
protonation
Protons
Pyridines - chemistry
pyridyl amine oxides
solubilization
Solutions
Surface-Active Agents - chemistry
surfactant
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Summary: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.
ISSN:1345-8957
1347-3352
1347-3352
DOI:10.5650/jos.62.123