The prediction of ¹³C chemical shifts can be challenging with density functional
theory (DFT). In this study 39 different functionals and 3 different basis sets were tested on three neutral alkylpyrroles and their corresponding protonated species. The calculated shielding constants were compared to experimental data and results from previous calculations at the MP2. We find that the meta-hybrid functional TPSSh with either the Pople style basis set 6-311++G(2d,p) or the polarization consistent basis set pcSseg-1 gives the best results for the ¹³C chemical shifts, whereas for the ¹H chemical shifts it is the TPSSh functional with either the 6-311++G(2d,p) or pcSseg-2 basis set. Including an explicit solvent molecule hydrogen bonded to NH in the alkylpyrroles improves the results slightly for the ¹³C chemical shifts. On the other hand, for ¹H chemical shifts the opposite is true. Compared to calculations at the MP2 level none of the DFT functionals can compete with MP2 for the 13C chemical shifts but for the ¹H chemical shifts the investigated DFT functionals are shown to give better agreement with experiment than MP2 calculations.