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Ubiquinone supports two distinct anionic states: a valence state and a non\u2010valence, dipole\u2010bound state. Dipole\u2010bound states, where an excess electron is weakly bound by the molecular dipole, are of significant interest as potential doorway states for electron transfer processes. In this work, we employ the electron\u2010attachment variant of the second\u2010order approximate coupled\u2010cluster (CC2) method to investigate the anionic states of ubiquinone analogues, Q\n                    <jats:sub>0<\/jats:sub>\n                    and Q\n                    <jats:sub>1<\/jats:sub>\n                    . We characterize the conformational energy, molecular dipole, and dipole\u2010bound state and valence state binding energies as a function of the two relevant coordinates of the system, which are the dihedral angles between the methoxy groups and the benzene ring. We find that the vertical electron affinity of the valence state varies by  over thermally accessible regions, whereas the dipole\u2010bound state appears discontinuously, governed by both dipole magnitude and orientation. Addition of a single isoprenoid unit to Q\n                    <jats:sub>0<\/jats:sub>\n                    , resulting in Q\n                    <jats:sub>1<\/jats:sub>\n                    , modestly reshapes the regions that support the dipole\u2010bound state, but leaves the valence state surface essentially unchanged. Cluster scans with small molecules (, HF, , and ) placed along the quinone dipole axis show that intermolecular interactions can modulate the electron affinity of the valence state by up to , far exceeding conformational tuning. The binding energy of the dipole\u2010bound state is enhanced or quenched depending on dipole alignment. Larger cluster models focusing on bacterial reaction center  reproduce the experimental finding that mutating an aliphatic isoleucine near the quinone to polar side chains leads to  lower electron affinity, while mutation to the also hydrophobic valine leaves the electron affinity unchanged. Our results demonstrate how the biological and chemical environments can modulate the electron\u2010accepting properties of ubiquinone and contribute to the discussion about the possible existence of dipole\u2010bound anions in biological environments. Our findings highlight the interplay between molecular conformation, intermolecular interactions, and electronic structure in determining the redox properties of biologically relevant molecules.\n                  <\/jats:p>","DOI":"10.1002\/jcc.70406","type":"journal-article","created":{"date-parts":[[2026,6,25]],"date-time":"2026-06-25T14:22:12Z","timestamp":1782397332000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["The Anionic States of Ubiquinone Characterized by Second\u2010Order Approximate Coupled\u2010Cluster Theory"],"prefix":"10.1002","volume":"47","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-7777-2911","authenticated-orcid":false,"given":"Mauro","family":"Gasc\u00f3n","sequence":"first","affiliation":[{"name":"Department of Chemistry KU Leuven  Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0006-2428-7669","authenticated-orcid":false,"given":"Robin E.","family":"Moorby","sequence":"additional","affiliation":[{"name":"Department of Chemistry KU Leuven  Leuven Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5919-424X","authenticated-orcid":false,"given":"Thomas\u2010C.","family":"Jagau","sequence":"additional","affiliation":[{"name":"Department of Chemistry KU Leuven  Leuven 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