title: Retention behavior of pyridinium oximes on PFP stationary phase in high-performance liquid chromatography.
abstract: The chromatographic behavior was studied of a series of potential acetylcholinesterase reactivators, pyridinium oximes, bearing linear aliphatic chains of the length of the aliphatic bridge from 1 to 12 carbon atoms, on a pentafluorophenyl-modified stationary phase. The retention mechanisms and the dependence of the capacity factor on mobile phase composition, aliphatic chain bridge length and calculated log P were evaluated and discussed in detail. The separation of the studied oximes was found to be driven by hydrophobic interactions when a lower content of organic modifier was used in mobile phase; however, the ion-exchange mechanism was the leading one when a large portion of organic modifier was used. In addition, the lipophilicity was found to be a driving mechanism of the separation of oximes bearing a connecting chain of the length of 6-12 carbon atoms, whereas the retention of oximes with shorter connecting chains was significantly influenced by other separation mechanisms such as aromatic or π-π interaction. These results can be useful for the development of new, efficient acetylcholinesterase reactivators.
authors.affiliation: 1Department of Chemistry, Faculty of Science, University of Hradec Kralove, Rokitanskeho 62, 50003 Hradec Kralove, Czech Republic.
authors.forename: Vlastimil
authors.initials: V
authors.lastname: Dohnal
authors.forename: Kamil
authors.initials: K
authors.lastname: Musílek
authors.forename: Kamil
authors.initials: K
authors.lastname: Kuča
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D005464:Fluorobenzenes / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D011726:Pyridinium Compounds / Q000737:chemistry*; D012044:Regression Analysis; D005466:Fluorocarbons
chemical_list: D005464:Fluorobenzenes; D010091:Oximes; D010636:Phenols; D011726:Pyridinium Compounds; C085539:2,3,4,5,6-pentafluorophenol; D005466:Fluorocarbons