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Interactions between surfactants, and the resultant ordering of surfactant assemblies, can be tuned by the appropriate choice of head- and tailgroups. Detailed studies of the ordering of monolayers of long-chain n-alkanoic and n-alkanol monolayers at the water-vapor interface have demonstrated that rigid-rod all-trans ordering of the tailgroups is maintained upon replacing the alcohol with a carboxylic acid headgroup. In contrast, at the water-hexane liquid-liquid interface, we demonstrate that substitution of the -CH(2)OH with the -COOH headgroup produces a major conformational change of the tailgroup from disordered to ordered. This is demonstrated by the electron density profiles of triacontanol (CH(3)(CH(2))(29)OH) and triacontanoic acid (CH(3)(CH(2))(28)COOH) monolayers at the water-hexane interface, as determined by X-ray reflectivity measurements. Molecular dynamics simulations illustrate the presence of hydrogen bonding between the triacontanoic acid headgroups that is likely responsible for the tail ordering. A simple free energy illustrates the interplay between the attractive hydrogen bonding and the ordering of the tailgroup.

Tail Ordering Due to Headgroup Hydrogen Bonding Interactions in Surfactant Monolayers at the Water−Oil Interface