α-Aminophosphonates 4-XC(6)H(4)–NH–CH(4-BrC(6)H(4))–P(O)(OiPr)(2) (X = H, Br, MeO): Crystal structures, Hirshfeld surface analysis, computational studies and in silico molecular docking with the SARS-CoV-2 proteins

Alkhimova, Larisa E.; Babashkina, Maria G.; Safin, Damir A.

We report structural and computational studies of three α-aminophosphonates 4-XC(6)H(4)–NH–CH(4-BrC(6)H(4))–P(O)(OiPr)(2), namely diisopropyl((4-bromophenyl)(phenylamino)methyl)phosphonate (X = H, 1), diisopropyl((4-bromophenyl)((4-bromophenyl)amino)methyl)phosphonate (X = Br, 2) and diisopropyl((4-bromophenyl)((4-methoxyphenyl)amino)methyl)phosphonate (X = MeO, 3). The structures of 1–3 were fully confirmed by means of the (31)P{(1)H} and (1)H NMR spectroscopy. Crystal structures of 2 and 3 are isostructural and each contain two independent molecules in the asymmetric unit cell. Energy frameworks have been calculated to analyze the overall crystal packing of 1–3. The DFT calculations were performed to verify the structures of 1–3 as well as its electronic and optical properties. Molecular docking was applied to examine the influence of both the (S)- and (R)-enantiomers of 1–3 on a series of the SARS-CoV-2 proteins.