Isosterism in pyrrole via azaboroles substitution, a theoretical investigation for electronic structural, stability and aromaticity

Abstract

This work uses ab-initio CBS-QB3 and density functional theory (B3LYP) to analyze the structure, stability, and aromaticity of all isosteric nitrogen-boron pyrroles. The mono-NB unit substituted group of the isosteric NB pyrrole has four isosteres, whereas the multi-NB unit substituted group has two isosteres. These two groups make up all isosteric NB pyrrole. For structural, energetic, magnetic, and electron delocalization criteria, the results highlight the predominance of the PN3B2 isostere and its greater stability over other conformers. In addition, the global reactivity indices, ESP, HOMO-LUMO, and NBO charges have all been estimated to forecast the active side's electron donation and acceptance. These isosteres are categorized as weak electrophiles and marginal nucleophiles. NB-isosteres have poorer stability, HOMO-LUMO gap, and aromaticity than the parent (pyrrole). In general, NB compounds with more ring sharing are less aromatic than NB molecules with less ring sharing. The current study is anticipated to help in understanding of the chemistry of NB substituted molecules and their experimental identification and characterization.

Keywords

• N-B doping
• Isosteres
• Aromaticity
• DFT
• Stability and azaboroles