Synthesis of novel amphiphilic N-alkylpyridinium salts

ORGN 148

James H. Wynne, jwynne@ccs.nrl.navy.mil and Arthur W. Snow. Chemistry Division, Naval Research Laboratory, 4555 Overlook AVE, SW, Washington, DC 20375
N-Alkylpyridinum salts are compounds that have found utility as phase transfer catalysts and in drug delivery processes. They are also known to possess antiseptic properties. We report the synthesis of a homologous series of surface active amphiphilic N-alkylpyridinium salts. They are functionalized with a monodisperse oxyethylene oligomeric chain which regulates the hydrophilic-hydrophobic balance and water solubility. The series includes molecules depicted below, where m = 6, 8 and n = 1, 2, 3, 4. The design, synthesis, purification and characterization of this series of compounds will be described.