Effect of the bifunctionalization of aminomethylphosphonic acid on the structural, electronic, vibrational, thermodynamic and antioxidant activity : Microwave-assisted synthesis, Density Functional Theory studies and DPPH radical scavenging activity

We report here a practical and efficient synthesis of alpha-aminotrismethylphosphonic acid (ATMP) from (Aminomethyl)phosphonic acid (AMPA) under green conditions using microwave irradiation, via IraniMoedritzer reaction. The ATMP was characterized by FT-IR, H-1 NMR, C-13 NMR, P-31-NMR and Elemental Analysis. It was found that the synthesis method gave a higher yield within very short reaction times in comparison with conventional method. In order to know the effect of phosphonomethylation moiety on the structures, electronic, vibrational and thermodynamic and optical properties for AMPA and ATMP molecules were carried out by DFT calculations in gas and water phases. Indeed, stable structures of the two molecules were optimized by using the hybrid B3LYP/6-31 G method and their HOMO-LUMO energy, MESP, global and local reactivity descriptors and NLO properties were calculated. Moreover, antioxidant activity of both investigated compounds was evaluated by DPPH center dot radical scavenging methods where a strong activity has been found. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

A practical and efficient synthesis of alpha-aminotrismethylphosphonic acid (ATMP) from (Aminomethyl)phosphonic acid (AMPA) under green conditions using microwave irradiation was reported in this study. The method showed higher yield in a shorter reaction time compared to conventional methods. Additionally, DFT calculations were used to study the structures, electronic, vibrational, thermodynamic, and optical properties of AMPA and ATMP molecules.