Effect of C–H ⋯ S and C–H ⋯ Cl interactions on the conformational preference of inhibitors of TIBO family

abstract n-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs) are an important class of drugs employed in antiviral therapy. The coordinates of three inhibitors, derived from TIBO, tetrahydroimidazo-(4,5,1-1-jk)(1,4)-benzodi-azepin-2(1H)-one (which belongs to the NNRTIs class), were taken from PDB database and the electronic structure were investigated by using the B3LYP/6-31+G(d,p) model. Results obtained by means of the natural bond orbital (NBO) and atoms in molecules (AIM) methods indicated the presence of weak hydrogen bonds of the C–H ⋯ S and C–H ⋯ Cl type, which are partially responsible for the conformational differences observed between the inhibitors 8 Cl-TIBO and 9 Cl-TIBO.