Building Chemical Intuition about Physicochemical Properties of C8-Per-/Polyfluoroalkyl Carboxylic Acids through Computational Means

We have predicted acid dissociation
constants (pKa), octanol–water
partition coefficients (KOW), and DMPC
lipid membrane–water partition
coefficients (Klipid‑w) of 150
different eight-carbon-containing poly-/perfluoroalkyl carboxylic
acids (C8-PFCAs) utilizing the COnductor-like Screening MOdel for
Realistic Solvents (COSMO-RS) theory. Different trends associated
with functionalization, degree of fluorination, degree of saturation,
degree of chlorination, and branching are discussed on the basis of
the predicted values for the partition coefficients. In general, functionalization
closest to the carboxylic headgroup had the greatest impact on the
value of the predicted physicochemical properties.