A biomimetic strategy was employed in the development of oxoanion-sele
ctive ionophores containing the guanidinium functional group. These io
nophores mimic the selective interaction observed between arginine res
idues of proteins and oxoanions. In previous work, it was demonstrated
that a structurally rigid guanidinium ionophore exhibited excellent h
ydrogen sulfite selectivity (Anal, Chem. 1994, 66, 3188-3192). Herein,
we describe guanidinium-containing ionophores that are selective for
the oxoanion salicylate. The ability to rationally design anion-select
ive electrodes through this biomimetic strategy, and to both alter sel
ectivity and improve response characteristics through structural chang
es to the ionophore, has been demonstrated. H-1-NMR complexation and m
odeling studies were used to examine and correlate the selectivity obs
erved with the structure of the guanidinium compounds.