Symmetry-adapted perturbation theory (SAPT) calculations are carried out to elucidate the intermolecular interactions present between fluorinated and nonfluorinated alkyl chain groups and aromatic pi systems in the folded and unfolded conformers of Wilcox torsion balance systems. The calculations predict the folded conformers to be 2.0-2.3 kcal/mol more stable than the unfolded conformers, with the preference for the folded conformer being greater in the fluorinated alkyl chain case. We also establish that a simple electrostatic analysis, based on atomic charges, is inadequate for understanding the conformational preferences of these systems. In the folded conformers, there are sizable charge penetration contributions that are not recovered by point charge models. Additionally, the SAPT analysis reveals that exchange repulsion interactions make a significant contribution to the relative stability of the folded and unfolded conformer.