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Reaction Gibbs free energies at room temperature were obtained using the B3LYP functional together with a continuum solvation model for water. From these data, acidity constants (pKa) and tautomerization constants (pKT) were calculated for the electronic ground state (S0) and the lowest excited singlet state (S1). The results reveal a pronounced dependence of both equilibria on the position of the hydroxy substituents. Upon photoexcitation, the compounds become considerably stronger acids and indicate, in many cases, a shift toward the keto tautomers rather than the parent enol forms. Moreover, our results support the feasibility of proton transfer from a hydroxy group on one aromatic ring to the adjacent ring via the central \u2212CH\u2550CH\u2013 bridge. Such processes may be relevant for nonradiative de-excitation pathways and for the protective biochemical functions of these compounds in plants.<\/jats:p>","DOI":"10.1021\/acsomega.6c06306","type":"journal-article","created":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T16:02:12Z","timestamp":1786204932000},"page":"50357-50365","source":"Crossref","is-referenced-by-count":0,"title":["Thermodynamics\nof Acidity and Photoacidity in\n                    <i>trans<\/i>\n                    -Resveratrol\nAnalogues: The Role of Prototropic Tautomerism"],"prefix":"10.1021","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0009-0002-1493-3592","authenticated-orcid":true,"given":"Andrea","family":"Kova\u0301c\u030cova\u0301","sequence":"first","affiliation":[{"name":"Slovak University of Technology in Bratislava , , Radlinske\u0301ho 9 , ,","place":["Bratislava, Slovakia, SK-812 37"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Michali\u0301k","sequence":"additional","affiliation":[{"name":"Slovak University of Technology in Bratislava , , Radlinske\u0301ho 9 , ,","place":["Bratislava, Slovakia, SK-812 37"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2301-9735","authenticated-orcid":true,"given":"Vladimi\u0301r","family":"Lukes\u030c","sequence":"additional","affiliation":[{"name":"Slovak University of Technology in Bratislava , , Radlinske\u0301ho 9 , ,","place":["Bratislava, Slovakia, SK-812 37"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,8]]},"reference":[{"key":"2026083119124846900_cit1","doi-asserted-by":"publisher","first-page":"2935","DOI":"10.3390\/plants12162935","article-title":"Resveratrol and\nOther Natural Oligomeric Stilbenoid Compounds and Their Therapeutic\nApplications","volume":"12","author":"Duta-Bratu","year":"2023","journal-title":"Plants"},{"key":"2026083119124846900_cit2","doi-asserted-by":"publisher","first-page":"11773","DOI":"10.1021\/jf8017707","article-title":"Ripening and Genotype\nControl Stilbene Accumulation in Healthy Grapes","volume":"56","author":"Gatto","year":"2008","journal-title":"J. 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Elektrochem."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.6c06306","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/33\/50357\/66465193\/acsomega.6c06306.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/11\/33\/50357\/66465193\/acsomega.6c06306.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,31]],"date-time":"2026-08-31T23:12:53Z","timestamp":1788217973000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/11\/33\/50357\/5250715\/Thermodynamics-of-Acidity-and-Photoacidity-in"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,8]]},"references-count":34,"journal-issue":{"issue":"33","published-online":{"date-parts":[[2026,8,8]]},"published-print":{"date-parts":[[2026,8,25]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.6c06306","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,8]]}}}