Vesicular Properties of Stereoisomeric Surfactants

• Published in: Langmuir Vol. 12; no. 24; pp. 5803 - 5808
• Main Authors: Jaeger, David A, Kubicz-Loring, Elzbieta, Price, Robert C, Nakagawa, Hiroko
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 27-11-1996
• Subjects: Chemistry; Colloidal state and disperse state; Exact sciences and technology; General and physical chemistry; Membranes; Vesicle; Anionic surfactant; Differential scanning calorimetry; Stereoisomer; Experimental study
• ISSN: 0743-7463; 1520-5827
• DOI: 10.1021/la960482l

All of the stereoisomeric forms of the surfactant, sodium 3-[2-methyl-4,5-bis(hexadecyloxymethyl)-1,3-dioxolan-2-yl]propane-1-sulfonate, have been prepared:  the enantiomers (+)-1 and (−)-1, the racemate (±)-1 (by two different methods), and meso 2 and meso 3. Vortexed vesicles of these materials were characterized by dynamic laser light scattering, to give vesicle sizes, and by differential scanning calorimetry, to give bilayer phase transition temperatures and associated enthalpies. Different calorimetry results were obtained for (+)-1 [(−)-1], (±)-1, 2, and 3. In particular, a comparison of the results for (+)-1 [(−)-1] and (±)-1 indicated the operation of enantiomer discrimination. The criteria of the “absolute” method of stereochemistry applied to this study were not completely fulfilled.