Fluorinated carboxylic acids and their radicals are becoming more prevalent in environmental waters and soils as they have been produced and used for numerous commercial applications. Understanding the thermochemical properties of fluorinated carboxylic acids will provide insights into the stability and reaction paths of these molecules in the environment, in body fluids, and in biological and biochemical processes. Structures and thermodynamic properties for over 50 species related to fluorinated carboxylic acids with two and three carbons are determined with density functional computational calculations B3LYP, M06-2X, and MN15 and higher ab initio levels CBS-QB3, CBS-APNO, and G4 of theory. The lowest energy structures, moments of inertia, vibrational frequencies, and internal rotor potentials of each target species are determined. Standard enthalpies of formation, ΔfH298°, from CBS-APNO calculations show the smallest standard deviation among methods used in this work. ΔfH298° values are determined via several series of isodesmic and/or isogyric reactions. Enthalpies of formation are determined for fluorinated acetic and propionic acids and their respective radicals corresponding to the loss of hydrogen and fluorine atoms. Heat capacities as a function of temperature, Cp(T), and entropy at 298 K, S298°, are determined. Thermochemical properties for the fluorinated carbon groups used in group additivity are also developed. Bond dissociation energies (BDEs) for the carbon-hydrogen, carbon-fluorine, and oxygen-hydrogen (C-H, C-F, and O-H BDEs) in the acids are reported. The C-H, C-F, and O-H bond energies of the fluorinated carboxylic acids are in the range of 89-104, 101-125, and 109-113 kcal mol-1, respectively. General trends show that the O-H bond energies on the acid group increase with the increase in the fluorine substitution. The strong carbon fluorine bonds in a fluorinated acid support the higher stability of the perfluorinated acids in the environment.