Evaluating the nature of binding of kerogen with clays and other minerals in oil shale is of critical importance for developing improved processes for extraction of oil from oil shale. The kerogen structure is complex, and we have identified three important kerogen moieties with structures similar to those identified in oil shale. Three moieties (pyridine, heptylamine and quinaldine) which are liquid in room temperature are chosen for the interaction study with Na-montmorillonite. Here, we report the results of Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD) and molecular dynamics simulation of the mixture of Na-montmorillonite with the moieties. Results from XRD are used to find the d-spacing of the clay interlayer with the maximum number of intercalated kerogen moieties into the clay interlayer for construction of representative clay-moiety models. Our FTIR and molecular dynamics simulation results indicate that there are significant non-bonded interactions of Na-montmorillonite with pyridine and heptylamine. No significant interaction of Na-montmorillonite with quinaldine was observed. Simulations indicate that the nonbonded interactions observed experimentally through shifts in IR bands are primarily electrostatic in nature. Identifying the nature of the interactions is important for future design of methodologies for economical and environmentally safe oil extraction from oil shale through cession of kerogen from minerals. (C) 2014 Elsevier Ltd. All rights reserved.