This study aims to provide simple but reliable theoretical model for monomer selection for molecular imprinting towards detection of nitroaromatic compounds. Presented data show that molecular imprinted polymer/non-imprinted polymer (MIP/NIP) system can be characterized sufficiently by use of very simple model. This model provides detailed description (qualitative and quantitative) regarding hydrogen bonding between the template and polymeric matrix hence can become good theoretical tool for monomer selection. Ab initio DFT (Density Functional Theory) method has been applied for structural, solvent, and vibrational frequency calculations. Binding energy and IR spectra have been carefully evaluated. Additionally, experimental FT-IR spectroscopy has been conducted to validate the formation of hydrogen bonding between studied species. (C) 2010 Elsevier Ltd. All rights reserved.