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Despite that, aromaticity still lacks a precise definition, leading to the use of various descriptors to quantify it. In this work, we employ a new set of six descriptors (ACS Omega 2025,\n                    <jats:bold>10<\/jats:bold>\n                    , 14157) built from components of the quadrupole moment  tensor from the Stone's Distributed Multipole Analysis (DMA) to examine the aromaticity trends in monosubstituted benzene derivatives (, , , , , , , , and ) and\n                    <jats:italic>para<\/jats:italic>\n                    \u2010homodisubstituted analogs (, , , , , and ). The  tensor is the first term in the DMA electric multipole expansion to include out\u2010of\u2010plane electron density contributions. Using a machine learning clustering technique, we identified four groups of molecules: neutral with minimal  variation, neutral with strong  perturbation ( and ), positively, and negatively charged species. Comparisons with the traditional aromaticity descriptors , , , , , and  were carried out. Among the \u2010based descriptors, , which is computed 1\u2009\u00c5 above the ring plane, exhibited the highest correlation with those descriptors, though small (). All the \u2010based descriptors reproduced the same trends of the traditional indices, except for the negative substituents, which were only correctly described by the former ones. We found that \u2010based descriptors correlated with ionization potentials (), electron affinities (), electronegativities (), electrophilicity indexes (), and electron\u2010donating\/accepting power (, ), but not with the chemical hardness (). In contrast, , , , and  correlated only with , while  and  showed no correlation. Therefore, our results show that the \u2010based descriptors reflect the \u03c0\u2010electron delocalization characteristic of aromaticity and also can describe frontier\u2010orbital reactivity trends.\n                  <\/jats:p>","DOI":"10.1002\/jcc.70257","type":"journal-article","created":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T04:45:31Z","timestamp":1762145131000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Aromaticity of Substituted Benzene Derivatives Employing a New Set of Aromaticity Descriptors Based on the Partition of Electron Density"],"prefix":"10.1002","volume":"46","author":[{"given":"Matheus","family":"M\u00e1ximo\u2010Canadas","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica  Rio de Janeiro Rio de Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nath\u00e1lia M. P.","family":"Rosa","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica  Rio de Janeiro Rio de Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8492-1223","authenticated-orcid":false,"suffix":"Jr","given":"Itamar","family":"Borges","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica  Rio de Janeiro Rio de Janeiro Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,11,2]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1511\/2015.112.18"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/sci4020024"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781119085928.ch4"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CP90088G"},{"key":"e_1_2_9_6_1","first-page":"204","article-title":"Quantum\u2010Theoretical Contributions to the Benzene Problem. 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