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Abstract: Triazine herbicides were used as model templates for a basic study of the molecular recognition process in imprinted polymers. These templates have the benefit of being structurally similar in the hydrogen bonding part while possessing widely different basicities and hydrophobicities This facilitates a systematic evaluation of me influence of the hydrophobic effect and the strength of hydrogen bonding between monomer and template, on the molecular recognition properties of the materials. If these effects contribute specifically to the observed recognition a change in solvent composition in the rebinding step is expected to change the driving force in this process. In aqueous-poor solvent systems we found that the selectivity for the template increased with its Broensted basicity whereas in aqueous-rich systems, affinity and selectivity increased with template hydrophobicity. An analogy is found in the specific hydrophobic effect often present in the binding of small molecules to biological macromolecules