Phosphonylated p-aminophenol derivatives: Microwave Assisted Synthesis, Density Functional Theory study and biological activities evaluation

A series of three alpha-aminomethylphosphonates have been synthesized in excellent yields, via Kabachnik-Fields reaction, under different conditions, at reflux heating and under microwave irradiations, by condensation of 4-aminophnol, trimethylphosphite and various aromatic aldehydes. The structures of the obtained compounds were confirmed by Elemental analysis, UV-vis, FT-IR, H-1-NMR and P-31-NMR spectra. Then, we present a detailed DFT study, based on B3LYP/6-31G(d,p) level of theory, of geometrical structures, vibrational, electronic properties of these compounds in order to make comparative study between these molecules. The Density Functional Theory method was beneficially used to analyze the HOMO-LUMO molecular orbitals and to calculate the energy gap (Delta E), Ionization potential (IP), Electron Affinity (EA), Global Hardness (eta), Chemical Potential (mu) and Global Electrophilicity (omega). The title compounds were screened for their antibacterial activity. All the title compounds exhibited promising antibacterial activity.

Automated summary

A series of alpha-aminomethylphosphonates were synthesized successfully via the Kabachnik-Fields reaction using different conditions including reflux heating and microwave irradiation. The compounds were characterized by various analytical techniques such as elemental analysis, UV-vis, FT-IR, H-1-NMR, and P-31-NMR. Density Functional Theory (DFT) was employed to study their molecular properties. The synthesized compounds exhibited promising antibacterial activity.