Binding patterns and H-1 NMR chemical shifts in the complexes of protonated N-(4-hydroxylphenyl)imidazole (g1), N-(4-aminophenyl)imidazole (g2), 2-phenylimidazole (g3) guests with cucurbit[6]uril (CB[6]), and symsubstituted tetramethyl cucurbit[6]uril (TMeCB[6]) in the gas phase as well as in water have been investigated using the density functional theory. It has been shown that the inclusion complexes or g1 and g2 with CB[6] or TMeCB[6] exhibit selective encapsulation of the phenyl moiety with its substituents binding to portal oxygens on the lower rim of the host and imidazole protons facilitate C-H center dot center dot center dot O interactions externally with upper rim ureido oxygens. On the other hand, the lowest-energy g3 complex encapsulates the imidazole ring within the host, engendering N-H center dot center dot center dot O interactions with portal oxygcns on the upper rim of the host with the phenyl ring residing outside the cavity owing to an absence or para-substituent and show qualitatively different host-guest binding patterns. Calculated H-1 NMR: spectra of the complexes in water reveal shielding of phenyl ring protons within die host cavity which exhibit signals at 0.2-0.5 ppm, whereas the protons of the imidazole ring participating in hydrogen hooded interactions exhibit deshielding. and the corresponding H-1 NMR signals are downshifted by 1.1-1.5 ppm in the spectra compared to those in the unbound guest, ill NMR chemical shifts of inclusion complexes thus obtained are in consonant with delta H patterns observed in experiments reported in the literature.