From this analysis we were able to identify and quantify competing effects due to cavity formation, van der Waals stabilization within the C 12 E 6 monolayer, as well as mostly compensating energetic and entropic effects due to DS -head group water-desolvation, and their contributions to the synergistic effect. In the case of DS - binding to the air-C 12 E 6 -water interface, we find the dominant stabilizing effect to be due to van der Waals stabilization within the monolayer. Further systematic analyses of free energy decomposition components may lead to theoretical design principles that allowing for the prediction of materials with desired properties. Specifically, the synergistic contributions on interfacial binding will likely be very sensitive to the length of the hydrophobic tail as well as the charge and chemistry of the head. In the future, it would be interesting to explore free energy decompositions within this context.