We report a solid-state O-17 NMR study of several crystalline carboxylic acids. We found that, while each of these compounds forms discrete hydrogen-bonded dimers in the crystal lattice, their solid-state O-17 magic-angle spinning (MAS) NMR spectra display quite different features and different temperature dependencies. We showed that experimentally observed O-17 NMR spectral behaviors can be explained as being due to thermal averaging between the two tautomers that are produced as a result of concerted double-hydrogen hopping dynamics within each dimer. In general, the two tautomers have different energies due to intramolecular interactions and crystal packing. From an analysis of variable-temperature O-17 MAS NMR spectra, energy asymmetry between the two tautomers was experimentally determined for each of the carboxylic acid compounds studied. The same data analysis also offers an opportunity to simultaneously assess O-17 NMR parameters in both low- and high-energy tautomers. We concluded that the periodic plane-wave density functional theory (DFT) calculations can produce reliable O-17 NMR parameters (chemical shift and quadrupolar coupling tensors) for both tautomers. The same periodic DFT calculations have also produced reasonable energy asymmetry values for the studied carboxylic acid dimers. We have also observed substantial H/D isotope shifts in solid-state O-17 NMR.