The purpose of this research is to synthesize and utilize chiral octyl isocyanates amino acid based surfactants. A mixture of an amino acid, sodium hydroxide and isocynates solvated in a mixture of acetone and water were mixed at room temperature for one hour. The product was easily separated from the reaction mixture via addition of HCl without the formation of any by-products. Purity of the product was confirmed using HPLC and NMR spectroscopy. A sequence of NMR water quenching studies in a predominantly basic solution showed that both amide groups were deprotonated, while a largely acidic solution showed both of the amide groups fully protonated. This amino acid isocyanate surfactant can be further investigated as to how the monomers form a micelle, how chiral ligands interact and separate in micellar electrokinetic chromatography and how their physical properties both differ from pervious amino acid terminated surfactants and kinetic interactions as a function of pH.

Effect of pH on isocynate amino acid based surfactants

249th National Meeting (2015)

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