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We investigate the effects of substituents using single\u2010reference (B3LYP\/DFT) and multireference (CASSCF\/MRCI) methods, focusing on structural (HOMA), vibrational (AI(vib)), topological (ELF<jats:sub><jats:italic>\u03c0<\/jats:italic><\/jats:sub>), electronic (MCI), magnetic (NICS), and stability (S<jats:sub>0<\/jats:sub>\u2013T<jats:sub>1<\/jats:sub> splitting) properties. The findings reveal that appropriate <jats:italic>\u03c0<\/jats:italic>\u2010electron\u2010donating and <jats:italic>\u03c0<\/jats:italic>\u2010electron\u2010accepting substituents with suitable size and symmetry can interact with the <jats:italic>\u03c0<\/jats:italic>\u2010system of the ring, significantly influencing <jats:italic>\u03c0<\/jats:italic>\u2010electron delocalization. While the charge factor has a minimal impact on <jats:italic>\u03c0<\/jats:italic>\u2010electron delocalization, the presence of a <jats:italic>p<\/jats:italic><jats:sub>z<\/jats:sub> orbital capable of interacting with the <jats:italic>\u03c0<\/jats:italic>\u2010electron delocalization is the primary factor leading to a deviation from the typical aromaticity characteristics observed in benzene.<\/jats:p>","DOI":"10.1002\/jcc.27296","type":"journal-article","created":{"date-parts":[[2023,12,28]],"date-time":"2023-12-28T17:33:40Z","timestamp":1703784820000},"page":"863-877","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["A multi\u2010descriptor analysis of substituent effects on the structure and aromaticity of benzene derivatives: \u03c0\u2010Conjugation versus charge effects"],"prefix":"10.1002","volume":"45","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9647-0821","authenticated-orcid":false,"given":"Julio C. 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