NMR chemical shift calculations (DFT-GIAO-B3LYP) on the 2-propyl cation in ion pairs were conducted for the C-s conformation (2) found earlier to be the energy minimum of the cation in the ion pair, as well as for the C-2 conformation (1), which is the energy minimum of the isolated cation. The level of the agreement between the isotropic chemical shift calculated with the dzvp basis set and the experiment increased with the increase in the calculated negative charge of the anion in the series HLiH-, H3BF-, BF4-, AsF6-, and SbF6-. The calculated charge and the agreeement with experiment also increased with the basis set to tzp for HBF3-, tzp and tz2p for BF4-, and to tzp, tz2p, qz2p, and pz(3)d for HF2-. The value calculated for the isolated ion was off by 20 ppm and did not improve from the dzvp to the pz3d level, which indicates that even in solution the cations are mostly ion-paired or, even more likely, move in aggegates of varying sizes. From the two conformations of the cation in the ion pair, 2.X- gave a better agreement at all levels, but 1.X- differed by less than the combined uncertainty of theory and experiment. Two of the three principal components, delta(11) and delta(33), were significantly off at all levels. Better to describe the system, a fragment of the ionic crystal was employed, placing two anions on the two sides of the cation and two to six LiF pairs at the remaining corners of a cubic structure, after the model of the crystal of the tert-butyl cation homologue. It was concluded that a good agreement of all parameters could be achieved for a placement of the LiF pairs between 2.8 Angstrom and 3.8 Angstrom from the center, but lacking the information about the crystal structure of the salt of the 2-propyl cation itself, the perfect match was not sought.