The partitioning of medium-chain fatty acid surfactants such as nonanoic acid (NA) between the bulk phase and the air/water interface is of interest to a number of fields including marine and atmospheric chemistry. However, questions remain about the behavior of these molecules, the contributions of various relevant chemical equilibria, and the impact of pH, salt and bulk surfactant concentrations. In this study, the surface adsorption of nonanoic acid and its conjugate base is quantitatively investigated at various pH values, surfactant concentrations and the presence of salts. Surface concentrations of protonated and deprotonated species are dictated by surface-bulk equilibria which can be calculated from thermodynamic considerations. Notably we conclude that the surface dissociation constant of soluble surfactants cannot be directly obtained from these experimental measurements, however, we show that molecular dynamics (MD) simulation methods, such as free energy perturbation (FEP), can be used to calculate the surface acid dissociation constant relative to that in the bulk. These simulations show that nonanoic acid is less acidic at the surface compared to in the bulk solution with a pK_a shift of 1.1 ± 0.6, yielding a predicted surface pK_a of 5.9 ± 0.6. A thermodynamic cycle for nonanoic acid and its conjugate base between the air/water interface and the bulk phase can therefore be established. Furthermore, the effect of salts, namely NaCl, on the surface activity of protonated and deprotonated forms of nonanoic acid is also examined. Interestingly, salts cause both a decrease in the bulk pK_a of nonanoic acid and a stabilization of both the protonated and deprotonated forms at the surface. Overall, these results suggest that the deprotonated medium-chain fatty acids under ocean conditions can also be present within the sea surface microlayer (SSML) present at the ocean/atmosphere interface due to the stabilization effect of the salts in the ocean. This allows the transfer of these species into sea spray aerosols (SSAs). More generally, we present a framework with which the behavior of partially soluble species at the air/water interface can be predicted from surface adsorption models and the surface pK_a can be predicted from MD simulations.