Description
1-Hexadecylpyridinium bromide is a cationic surfactant capable of bactericidal activity and has been used for ion exchange. As a bactericidal agent, it reduces the surface tension between pathogenic membranes and their environments. This interaction disrupts membrane integrity and osmoregulation, leading to cell lysis. It has also been shown to quickly and efficiently remove metal ions from solutions. The compound removes cations from the solution through a cation/surfactant complex, which precipitates from an aqueous phase into an organic phase and can subsequently be extracted. It is an effective ion exchange agent for extracting DNA and proteins.
Synthesis
General method: 1-bromohexadecane (0.01 mol) and pyridine (0.011 mol) were added sequentially to 25 mL of anhydrous acetonitrile and heated to reflux for 24 hours. Upon completion of the reaction, the solvent was removed by evaporation, the residue was co-evaporated with benzene to remove residual water, and finally the N-hexadecyl pyridine bromide salt was recrystallized from acetone.
References
[1] Molecules, 2010, vol. 15, # 3, p. 1967 - 1972
[2] Green Chemistry, 2009, vol. 11, # 1, p. 83 - 90
[3] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 46 - 55
[4] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1952, vol. 291, p. 1,4
[5] Journal of the American Pharmaceutical Association (1912-1977), 1942, vol. 31, p. 51
