Solid phase extraction is one of the most widely used techniques to trap and release compounds in a solution. A hydrophobic substance will stick efficiently to a hydrophobic surface (the “like dissolves like” principle). With an introduced response (i.e. pH change), a responsive surface can change from hydrophobic to hydrophilic, weakening the hydrophobic substance’s attraction and thus facilitate in an easy removal. A surface has been prepared having a terminal anthranilic acid (AA) moiety on silica gel particles, microscope slides, and TLC plates in three steps. First, a vinyl group was attached to the surface. Then, this vinyl group was reacted to form a surface carboxylic acid group. Finally, the carboxylic acid group was converted to an amide group that linked to the silica surface. FT-IR, and elemental analysis were used to confirm each step of the synthesis. At low pHs the –COOH group on the AA moiety is neutral and intrahydrogen bonding keeps this moiety’s phenyl (hydrophobic) portion exposed to the surface. The effect has been investigated by measuring contact angles at various pH values. At higher pHs the AA’s carboxylic acid group becomes the charged carboxylate, rendering the surface hydrophilic. Substances can be trapped and released using this unique switching approach. 2-naphthol, for example, is hydrophobic and thus was trapped at lower pHs (pH 4) (hydrophobic surface) and released at higher pHs (pH 10) (hydrophilic surface) on this responsive surface