Synthesis, spectroscopic characterization, anti-urease activities of a novel bisphosphoramidate, a combined experimental and computational study

Methylenebis(N,N'-dibenzylphosphoramidate) (MBDPA) is synthesized by 1:8 mol ratio reaction of Methylenebis(phosphonic dichloride) and benzylamine. MBDPA characterized by FT-IR, H-1 NMR, C-13 NMR, (PNMR)-P-31 spectroscopy. Also, The IC50 value for MBDPA is 5.23 nM that show very strong urease inhibitory activity. The geometry optimization is performed using the B3LYP and PBE1PBE density functional methods with two basis sets; 6-311 G (d, p) and 6-311 + G(d,p). H-1,C-13 and (PNMR)-P-31 chemical shifts have been calculated by using the gauge independent atomic orbital (GIAO) method. The infrared spectra of MBDPA are calculated and compared with the experimentally observed ones. The assignments are determined on the basis of the potential energy distribution of the all vibrational modes. Results of this study showed that there is a good correlation between the experimental data and computational results. The electronic structure is studied by analyzing the frontier molecular orbitals and molecular electrostatic potential for the prediction of stability and activity of the MBDPA. (C) 2018 Published by Elsevier B.V.