The conformational analysis of HIV-1 Reverse Transcriptase Inhibitor, nevirapine, 11-cyclopropyl-5,-11dihydro-4-methyl-6H-dipyrido[3,2-b2′,3′-e][1,4]diazepin-6-one, was investigated using ab initio and density functional theory calculations. The fully optimized structures and rotational potential energies of the nitrogen and carbon bonds in the cyclopropyl ring (C15-N11-C17-C19, α) were examined in detail. Geometries obtained from all applied calculations show similarities to the complex structure with HIV-1 reverse transcriptase. To obtain more information on the structure, conformational minima of nevirapine, optimized at the B3LYP/6-31G** level, were calculated for the ¹H, ¹³C, and ¹⁵N-NMR chemical shifts at the B3LYP/6-311++G** level using the GIAO approach in DMSO and chloroform IEFPCM solvation models. The calculated ¹H, ¹³C-NMR chemical shifts agree well with the experimental data, which indicates that the geometry of nevirapine in solution is similar to that of the molecule in the inhibition complex. Solvation free energies (ΔG _sol ) of nevirapine in DMSO and chloroform were also obtained.