Schleyer-type hyperconjugative aromaticity in CH isomers of diazoles revealed by DFT and NBO analysis.

ABSTRACT: Aromaticity is a central concept in organic chemistry, traditionally evaluated through structural, magnetic, and electronic criteria. In this study, density functional theory (DFT) calculations were performed to systematically investigate the impact of various substituents (-H, -Me, -CH₂-CH₂-, -F, -Cl, -SiH₃, -GeH₃, -NH₂, -OH, -BH₂, -CN) on the aromaticity of CH isomers of diazoles across four positional isomers (A-D). Aromaticity was quantified using the HOMED, BI, NICS(1), and NICS_zz(1) indices, while Natural Bond Orbital (NBO) analysis provided insights into charge distribution and second-order stabilization energies (E⁽²⁾). The results demonstrate that silyl and germyl substituents significantly enhance Schleyer-type hyperconjugati

SUBMITTER: Dehkordi PN 

PROVIDER: S-EPMC12921015 | biostudies-literature | 2026 Feb

REPOSITORIES: biostudies-literature