In this paper we present a computer simulation of chiral solvated dimers. The difference in the free energy, for two enantiomers, is in direct relationship with experimental results for chiral high performance liquid chromatography. Earlier work had shown the importance of sampling a substantial of solvated dimer conformations. Our main aim in this paper was to test methods for predicting the importance of each possible dimer conformation to the free energy at an early stage of the calculation and thus reduce the extensive computer time consumed by a full set of solvated simulations. As a model for chiral high performance liquid chromatography the stationary phase we have used a linked dimeric carbohydrate, and benzoin was used as a model chiral analyte. The solvent was tetrahydrofuran. The majority of the simulations were performed using molecular dynamics.