Fluid and Chiral Ephedrinium Myristate Micellar Fibers

Myristic acid crystallizes as 1:1 mixture with its sodium salt (acid soap) at pH 9.8, as pure sodium salt (soap) upon addition of sodium chloride and gives long fibers (curds) of a carboxylate monohydrate at pH 11.5. Transmission electron microscopy shows micellar fibers as structural units of the curds. Curvature of the myristate bilayer is enforced by hydration, not by repulsive forces between anions. Ephedrinium and pseudoephedrinium myristate produce stable isolated fibers of bimolecular thickness in water. They dissolve magnesium octaethylporphyrin in a chiral arrangement and show strong CD effects. The aqueous solution is viscoelastic. Twisted ribbons were obtained from the cationic analogue cetyltrimethylammonium with the chiral adenosine monophosphate counterion.