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

• Published in: Journal of molecular structure Vol. 1250; p. 131714
• Main Authors: Bouamrane, Omar Larbi, Hellal, Abdelkader, Hachama, Kamel, Touafri, Lasnouni, Haddadi, Ines, Layaida, Houdheifa, Kirouani, Imene, Hassani, Abdelkader, Mersellem, Mohamed, Madani, Abdelghani, Bensouici, Chawki
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-02-2022
• Subjects: DFT; DPPH; Fukui indices; Thermodynamic parameters; α-aminomethylphosphonylation; α-Aminophosphonic acid; Thermodynamic parameters; α-aminomethylphosphonylation; α-Aminophosphonic acid; DFT; DPPH; Fukui indices
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.131714

•Synthesis of α-aminotrismethylphosphonic acid from (Aminomethyl)phosphonic acid under microwave irradiation.•The possible optimized geometric structures of (ATMP) and (AMPA) were researched.•HOMO and LUMO energies, MESP distribution of the molecules were calculated.•Thermodynamic and optical parameters were determined.•Antioxidant activity of both investigated compounds was evaluated by DPPH. radical scavenging methods.
We report here a practical and efficient synthesis of α-aminotrismethylphosphonic acid (ATMP) from (Aminomethyl)phosphonic acid (AMPA) under green conditions using microwave irradiation, via Irani-Moedritzer reaction. The ATMP was characterized by FT-IR, 1H NMR, 13C NMR, 31P-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. radical scavenging methods where a strong activity has been found.
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