Mercuration and Telluration of 2-Fluoro-5-nitroaniline: Synthesis, Antibacterial, and Computational Study

Abstract

New derivatives of organotellurium and organomercury compounds have been synthesized in the reaction of 2-fluoro-5-nitroaniline with mercuric acetate and further with tellurium(IV) tetrabromide. Reaction of (4-amino-5-fluoro-2-nitrophenyl)tellurium(IV) tribromide with 4-hydroxyphenyl mercury(II) chloride gives asymmetrical diaryltellurium(IV) dibromide, whereas reaction of (4-amino-5-fluoro-2-nitrophenyl)mercury(II) chloride with phenol and 4-hydroxy benzaldehyde produces a new aryl mercury(II) chloride that contains the azomethine and azo groups. Reaction of aryl mercury(II) chloride with tellurium(IV) tetrabromide results in aryaltellurium(IV) tribromide furnished by the azomethine and azo groups. Reduction of unsymmetrical diaryltellurium(IV) dibromide and aryltellurium(IV) tribromide by hydrazine hydrate leads to the corresponding asymmetrical diaryltelluride and diarylditelluride. Structures of the new synthesized compounds are supported by FT-IR and 1H NMR spectra. Anti-bacterial activity of the new products has been tested against Klebsiella pneumonia Proteus, Escherichia coli, Pseudomonas spp., and Staphylococcus aureus. The compounds are characterized as highly active. The molecular structure level and energies of compounds have been computed through the Density Functional Theory (DFT).