This research examines the fundamental science behind the ligand-receptor binding interaction that occurs between nicotine and nicotinic acetylcholine receptors (nAChRs). The present focus is on the synthesis and evaluation of a series of dicarboxylic acid nAChR analogs for binding nicotine via two hydrogen bonds. Nicotine-receptor analog binding was assessed with ¹H-NMR, UV-Vis, fluorimetry, and isothermal titration calorimetry. Preliminary data suggest an interaction between the receptor analog and nicotine; the results will be disclosed here. Within a series, our receptor analogs contain subtle modifications that will permit design of an array of nAChR analogs to mimic the array of nAChRs found in nature. Such an array will provide pattern recognition data that can be applied to screening target compounds that interact with nAChRs.