We used a molecular mechanics/molecular dynamics computational method to simulate solvent swelling of the pyridine-insoluble (PI) fraction obtained from extraction of Upper Freeport bituminous coal, an Argonne premium coal sample. The effects of benzene and cyclohexane on swelling were examined and compared with previous results for methanol. A model structure for the PI fraction was placed in a periodic boundary cell. As solvent molecules were introduced into the cell, the potential energy of the PI-solvent system decreased and the volume of the cell increased up to the limiting number of solvent molecules-9 for benzene and 2 for cyclohexane-that could be added to produce stable structures. The contribution of the electrostatic interaction to the decrease in the total energy of the PI-solvent system was larger than those of the hydrogen bond and van der Waals interactions, regardless of the solvent used. Swelling ratios estimated from the ratio of the weight increase with the number of the solvent molecules introduced were in good agreement with the ratio determined experimentally from sorption data, and were much lower than ratios obtained from volumetric swelling measurements.