Contribution of sulfonyl-aromatic and sulfonic acid-aromatic interactions in novel sulfonyl/sulfonic acid-embedded reversed phase materials.
Two novel sulfonyl-embedded reversed phase materials with sulfonic acid moieties (SO(X)-RP) were prepared by a simple oxidation of two silica-based sulfur-embedded RP-phases (S-RP). The chromatographic behavior of the resultant sulfonyl/sulfonic acid-embedded phase C3-SO(2)-C18/SO(3)H and the sulfonyl-embedded phase C3-SO(2)-C14 e.c. (silanol endcapped) was extensively elucidated with a number of well-established as well as self-assembled column tests. These SO(X)-RP phases were also compared with their corresponding S-RP phases as well as with two commercial carbonyl-containing RP phases (CO-RP) with amide- and urea-embedding. The SO(X)-RP phases were found to exhibit exceptionally high planar recognition ability for polyaromatic analytes at comparable retention times to the investigated CO-RP phases and highly reduced retention compared to the parent, non-oxidized S-RP-materials. The results of this study suggest that the selectivity enhancement observed with the S-oxidized phases is due to sulfonyl-pi and sulfonic acid-pi interactions. Furthermore these novel SO(X)-RP phases proved to be fully applicable under 100% aqueous mobile-phase conditions making them a useful alternative to conventional RP as well as polar-embedded CO-RP phases.
Horak
Jeannie
J
Institute of Analytical Chemistry, University of Vienna, Waehringerstrasse 38, 1090 Vienna, Austria.
Lindner
Wolfgang
W
D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation* / Q000379:methods; D004355:Drug Stability; D007474:Ion Exchange; D009930:Organic Chemicals / Q000302:isolation & purification; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry*
D009930:Organic Chemicals; D011084:Polycyclic Aromatic Hydrocarbons; D013451:Sulfonic Acids