{"doi":"10.1002/qua.25504","title":"Electron affinity of modified benzene","abstract":"<jats:title>Abstract</jats:title><jats:p>The electron affinities of organic molecules obeying Hückel's rule of aromaticity are vanishingly small, if not negative. For example, benzene, a classic example of an aromatic molecule, has an electron affinity of −1.15 eV. Using density functional theory, we have systematically calculated the electron affinities and vertical detachment energies of C<jats:sub>6</jats:sub>H<jats:sub>6</jats:sub> by substituting H with halogen (F) and superhalogen (BO<jats:sub>2</jats:sub>) moieties, as well as replacing one of the C atoms with B. The ground state geometries were obtained by examining about 330 isomers. The electron affinities are found to steadily increase with these substitutions/replacements, even surpassing that of Cl, the element with the highest electron affinity in the periodic table, in the case of C<jats:sub>5</jats:sub>BH(BO<jats:sub>2</jats:sub>)<jats:sub>5</jats:sub>. In some special cases such as C<jats:sub>6</jats:sub>H<jats:sub>5</jats:sub>(BO<jats:sub>2</jats:sub>) the electron affinity and vertical detachment energy differ by as much as 5 eV, indicating substantial changes in the geometry as the electron is removed from the anion. We hope that the ability to change the negative electron affinity of C<jats:sub>6</jats:sub>H<jats:sub>6</jats:sub> to large positive values by substituting H and/or replacing C atom will motivate experimental studies.</jats:p>","journal":"International Journal of Quantum Chemistry","year":2018,"id":43207,"datarank":1.0428055652379882,"base_score":3.1354942159291497,"endowment":3.1354942159291497,"self_citation_contribution":0.47032413238937254,"citation_network_contribution":0.5724814328486156,"self_endowment_contribution":0.47032413238937254,"citer_contribution":0.5724814328486156,"corpus_percentile":null,"corpus_rank":null,"citation_count":22,"citer_count":21,"citers_with_citation_signal":18,"citers_with_endowment":18,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":205705,"name":"Purusottam Jena","orcid":null,"position":1,"is_corresponding":false},{"id":205704,"name":"Nicholas Driver","orcid":"0000-0002-3164-3178","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"base_score":3.1354942159291497,"endowment":3.1354942159291497,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"21464855","pmcid":null,"openalex_id":"https://openalex.org/W2760294055","authors":[],"funders":[{"funder_name":"U.S. Department of Energy","grant_id":"DE‐FG02‐96ER45579","title":null}],"total_grants":1,"fwci":1.1109,"citation_percentile":0.75263236,"influential_citations":0,"citation_trend":[{"year":2018,"count":4},{"year":2019,"count":4},{"year":2020,"count":1},{"year":2021,"count":4},{"year":2022,"count":2},{"year":2023,"count":3},{"year":2024,"count":2},{"year":2025,"count":2}],"oa_status":"green","license":"http://onlinelibrary.wiley.com/termsAndConditions#am","oa_locations":[{"url":"https://www.osti.gov/servlets/purl/1537623","host_type":"repository"},{"url":"https://www.osti.gov/biblio/1537623","host_type":"GREEN"},{"url":"https://www.osti.gov/servlets/purl/1537623","host_type":"repository"},{"url":"https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fqua.25504","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/pdf/10.1002/qua.25504","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/full-xml/10.1002/qua.25504","host_type":"publisher"},{"url":"https://onlinelibrary.wiley.com/doi/am-pdf/10.1002/qua.25504","host_type":"publisher"},{"url":"https://doi.org/10.1002/qua.25504","host_type":"journal"},{"url":"https://www.osti.gov/biblio/1416866","host_type":"repository"}],"fields_of_study":["Synthesis and Properties of Aromatic Compounds","Crystallography and molecular interactions","Advanced Chemical Physics Studies","Chemistry"],"mesh_terms":[],"keywords":["Electron affinity (data page)","Chemistry","Benzene","Affinities","Molecule","Halogen","Atom (system on chip)","Density functional theory","Ion","Electron","Proton affinity","Computational chemistry","Aromaticity","Crystallography","Binding energy","Stereochemistry","Atomic physics","Organic chemistry","Physics"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Affordable and clean energy"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-06-14T20:34:29.121623Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}