{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,9]],"date-time":"2026-05-09T06:32:39Z","timestamp":1778308359593,"version":"3.51.4"},"reference-count":45,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2025,3,1]],"date-time":"2025-03-01T00:00:00Z","timestamp":1740787200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2025,3,1]],"date-time":"2025-03-01T00:00:00Z","timestamp":1740787200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2025,3,1]],"date-time":"2025-03-01T00:00:00Z","timestamp":1740787200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2025,3,1]],"date-time":"2025-03-01T00:00:00Z","timestamp":1740787200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2025,3,1]],"date-time":"2025-03-01T00:00:00Z","timestamp":1740787200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2025,3,1]],"date-time":"2025-03-01T00:00:00Z","timestamp":1740787200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2025,3,1]],"date-time":"2025-03-01T00:00:00Z","timestamp":1740787200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Journal of Molecular Graphics and Modelling"],"published-print":{"date-parts":[[2025,3]]},"DOI":"10.1016\/j.jmgm.2024.108911","type":"journal-article","created":{"date-parts":[[2024,11,21]],"date-time":"2024-11-21T08:12:26Z","timestamp":1732176746000},"page":"108911","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":7,"special_numbering":"C","title":["Keto-enol Tautomerism of hydroxy-substituted arenes: Theoretical study and experimental consequences"],"prefix":"10.1016","volume":"135","author":[{"given":"Andrea","family":"Kov\u00e1\u010dov\u00e1","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Martin","family":"Michal\u00edk","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Horst","family":"Hartmann","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2301-9735","authenticated-orcid":false,"given":"Vladim\u00edr","family":"Luke\u0161","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.jmgm.2024.108911_bib1","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1002\/adma.201001402","article-title":"Rylene and related diimides for organic electronics","volume":"23","author":"Zhan","year":"2011","journal-title":"Adv. Mater."},{"key":"10.1016\/j.jmgm.2024.108911_bib2","doi-asserted-by":"crossref","first-page":"252","DOI":"10.2174\/138527212798993031","article-title":"Recent progress on organic semiconductors for thin-film field-effect transistors","volume":"16","author":"Zhang","year":"2012","journal-title":"Curr. Org. Chem."},{"key":"10.1016\/j.jmgm.2024.108911_bib3","series-title":"The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons","author":"Luch","year":"2005"},{"key":"10.1016\/j.jmgm.2024.108911_bib4","doi-asserted-by":"crossref","first-page":"507","DOI":"10.1016\/S0045-6535(00)00223-X","article-title":"Identification of surrogate compounds for the emission of PCDD\/F (I-TEQ value) and evaluation of their on-line realtime detectability in flue gases of waste incineration plants by REMPI-TOFMS mass spectrometry","volume":"42","author":"Blumenstock","year":"2001","journal-title":"Chemosphere"},{"key":"10.1016\/j.jmgm.2024.108911_bib5","doi-asserted-by":"crossref","DOI":"10.1016\/j.jclepro.2020.123094","article-title":"Emissions of particulate matters, volatile organic compounds and polycyclic aromatic hydrocarbons from warm and hot asphalt mixes","volume":"275","author":"Xiu","year":"2020","journal-title":"J. Clean. Prod."},{"key":"10.1016\/j.jmgm.2024.108911_bib6","series-title":"Smoking and Healt: Report of the Advisory Committee to the Surgeon General of the United States","first-page":"1","year":"1964"},{"key":"10.1016\/j.jmgm.2024.108911_bib7","doi-asserted-by":"crossref","DOI":"10.1016\/j.isci.2021.102865","article-title":"A light-switching pyrene probe to detect phase-separated biomolecules","volume":"24","author":"Hazawa","year":"2021","journal-title":"iScience"},{"key":"10.1016\/j.jmgm.2024.108911_bib8","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1093\/jat\/29.3.175","article-title":"Determination of phenanthrene and hydroxyphenanthrenes in various biological matrices at trace levels using gas chromatography-mass spectrometry","volume":"29","author":"Grova","year":"2005","journal-title":"J. Anal. Toxicol."},{"key":"10.1016\/j.jmgm.2024.108911_bib9","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1007\/s004200050216","article-title":"Elimination of 1-hydroxypyrene after human volunteer exposure to polycyclic aromatic hydrocarbons","volume":"70","author":"Brze\u017anicki","year":"1997","journal-title":"Int. Arch. Occup. Environ. Health"},{"key":"10.1016\/j.jmgm.2024.108911_bib10","doi-asserted-by":"crossref","first-page":"2853","DOI":"10.1897\/06-042R.1","article-title":"Metabolite production in degradation of pyrene alone or in a mixture with another polycyclic aromatic hydrocarbon by Mycobacterium sp","volume":"25","author":"Zhong","year":"2006","journal-title":"Environ. Toxicol. Chem."},{"key":"10.1016\/j.jmgm.2024.108911_bib11","first-page":"761","article-title":"Evaluation of exposure to polycyclic aromatic hydrocarbons in a coke production and a graphite electrode manufacturing plant: assessment of urinary excretion of 1-hydroxypyrene as a biological indicator of exposure","volume":"49","author":"Buchet","year":"1992","journal-title":"Br. J. Ind. Med."},{"key":"10.1016\/j.jmgm.2024.108911_bib12","doi-asserted-by":"crossref","first-page":"734","DOI":"10.1080\/15287390801985265","article-title":"New biomarkers of occupational exposure to polycyclic aromatic hydrocarbons","volume":"71","author":"Seidel","year":"2008","journal-title":"J. Toxicol. Environ. Health Part A Curr. Issues."},{"key":"10.1016\/j.jmgm.2024.108911_bib13","series-title":"Polycyclic Aromatic Hydrocarbons: Part I. Exposure","author":"Ifegwu","year":"2015"},{"key":"10.1016\/j.jmgm.2024.108911_bib14","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1111\/j.2164-0947.1974.tb01566.x","article-title":"Theory of carcinogenic activity of aromatic hydrocarbons","volume":"36","author":"Herndon","year":"1974","journal-title":"Trans. N. Y. Acad. Sci."},{"key":"10.1016\/j.jmgm.2024.108911_bib15","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1021\/ar50106a006","article-title":"Solution chemistry of arene oxides","volume":"9","author":"Bruice","year":"1976","journal-title":"Acc. Chem. Res."},{"key":"10.1016\/j.jmgm.2024.108911_bib16","first-page":"325","article-title":"Kinetic studies of keto\u2013enol and other tautomeric equilibria by flash photolysis","volume":"44","author":"Wirz","year":"2010","journal-title":"Adv. Phys. Org. Chem."},{"key":"10.1016\/j.jmgm.2024.108911_bib17","doi-asserted-by":"crossref","first-page":"605","DOI":"10.1139\/v99-048","article-title":"Ketonization equilibria of phenol in aqueous solution","volume":"77","author":"Capponi","year":"1999","journal-title":"Can. J. Chem."},{"key":"10.1016\/j.jmgm.2024.108911_bib18","doi-asserted-by":"crossref","first-page":"6633","DOI":"10.1021\/ja00541a075","article-title":"5H-Perfluoropentamethylcyclopentadiene, an extraordinary carbon acid","volume":"102","author":"Laganis","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.jmgm.2024.108911_bib19","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1021\/cr60249a001","article-title":"The chemistry of stable phenoxy radicals","volume":"67","author":"Altwicker","year":"1967","journal-title":"Chem. Rev."},{"key":"10.1016\/j.jmgm.2024.108911_bib20","doi-asserted-by":"crossref","first-page":"1040","DOI":"10.2174\/138955707782110105","article-title":"Michael acceptors as cysteine protease inhibitors","volume":"7","author":"Santos","year":"2007","journal-title":"Mini-Rev. Med. Chem."},{"key":"10.1016\/j.jmgm.2024.108911_bib21","doi-asserted-by":"crossref","first-page":"1723","DOI":"10.1021\/ja00058a016","article-title":"Acid-Catalyzed rearrangement of \u039a-region arene oxides: observation of ketone intermediates and a sterically induced change in rate-determining step","volume":"115","author":"Nashed","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.jmgm.2024.108911_bib22","doi-asserted-by":"crossref","DOI":"10.1016\/j.ibiod.2021.105233","article-title":"Bacterial degradation of pyrene: biochemical reactions and mechanisms","volume":"162","author":"Zada","year":"2021","journal-title":"Int. Biodeterior. Biodegrad."},{"key":"10.1016\/j.jmgm.2024.108911_bib23","doi-asserted-by":"crossref","first-page":"787","DOI":"10.1007\/s10532-014-9699-9","article-title":"Degradation of phenanthrene by the rhizobacterium Ensifer meliloti","volume":"25","author":"Muratova","year":"2014","journal-title":"Biodegradation"},{"key":"10.1016\/j.jmgm.2024.108911_bib24","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1007\/s13353-016-0380-3","article-title":"Polycyclic aromatic hydrocarbons and PAH-related DNA adducts","volume":"58","author":"Ewa","year":"2017","journal-title":"J. Appl. Genet."},{"key":"10.1016\/j.jmgm.2024.108911_bib25","series-title":"Gaussian 16, Rev. B.01","author":"Frisch","year":"2016"},{"key":"10.1016\/j.jmgm.2024.108911_bib26","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1007\/s00214-007-0310-x","article-title":"The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other function","volume":"120","author":"Zhao","year":"2008","journal-title":"Theor. Chem. Acc."},{"key":"10.1016\/j.jmgm.2024.108911_bib27","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1007\/BF00533485","article-title":"The influence of polarization functions on molecular orbital hydrogenation energies","volume":"28","author":"Hariharan","year":"1973","journal-title":"Theor. Chim. Acta"},{"key":"10.1016\/j.jmgm.2024.108911_bib28","doi-asserted-by":"crossref","first-page":"6378","DOI":"10.1021\/jp810292n","article-title":"Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions","volume":"113","author":"Marenich","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"10.1016\/j.jmgm.2024.108911_bib29","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1016\/j.jct.2016.04.005","article-title":"Gibbs energies of protonation and complexation of platinum and vanadate metal ions with naringenin and phenolic acids: theoretical calculations associated with experimental values","volume":"100","author":"Fazary","year":"2016","journal-title":"J. Chem. Thermodyn."},{"key":"10.1016\/j.jmgm.2024.108911_bib31","doi-asserted-by":"crossref","first-page":"4852","DOI":"10.1063\/1.477096","article-title":"Calculation of the aqueous solvation free energy of the proton","volume":"109","author":"Tawa","year":"1998","journal-title":"J. Chem. Phys."},{"key":"10.1016\/j.jmgm.2024.108911_bib32","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1016\/j.cplett.2016.03.004","article-title":"Quantum chemical approach for condensed-phase thermochemistry (III): accurate evaluation of proton hydration energy and standard hydrogen electrode potential","volume":"650","author":"Ishikawa","year":"2016","journal-title":"Chem. Phys. Lett."},{"key":"10.1016\/j.jmgm.2024.108911_bib33","series-title":"CRC Handbook of Chemistry and Physics","author":"Lide","year":"2004"},{"key":"10.1016\/j.jmgm.2024.108911_bib34","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.comptc.2013.06.031","article-title":"Computational calculation of absolute aqueous pKa values for phenols","volume":"1019","author":"Cunningham","year":"2013","journal-title":"Comput. Theor. Chem."},{"key":"10.1016\/j.jmgm.2024.108911_bib35","doi-asserted-by":"crossref","DOI":"10.3390\/molecules27238590","article-title":"An accurate approach for computational pKa determination of phenolic compounds","volume":"27","author":"Pezzola","year":"2022","journal-title":"Molecules"},{"key":"10.1016\/j.jmgm.2024.108911_bib36","doi-asserted-by":"crossref","first-page":"784","DOI":"10.1039\/b109242c","article-title":"Enol-keto tautomerism of 9-anthrol and hydrolysis of its methyl ether","volume":"2","author":"McCann","year":"2002","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"10.1016\/j.jmgm.2024.108911_bib37","doi-asserted-by":"crossref","first-page":"901","DOI":"10.1039\/c0pp00034e","article-title":"Flash photolytic generation of two keto tautomers of 1-naphthol in aqueous solution: kinetics and equilibria of enolization","volume":"9","author":"Gut","year":"2010","journal-title":"Photochem. Photobiol. Sci."},{"key":"10.1016\/j.jmgm.2024.108911_bib38","first-page":"3","article-title":"Diffusion-Controlled reactions in solution, compr","volume":"25","author":"Rice","year":"1985","journal-title":"Chem. Kinet."},{"key":"10.1016\/j.jmgm.2024.108911_bib39","doi-asserted-by":"crossref","first-page":"493","DOI":"10.1146\/annurev.pc.34.100183.002425","article-title":"Diffusion-controlled reactions","volume":"34","author":"Calef","year":"1983","journal-title":"Annu. Rev. Phys. Chem."},{"key":"10.1016\/j.jmgm.2024.108911_bib40","doi-asserted-by":"crossref","first-page":"568","DOI":"10.2174\/1570179414666161121124846","article-title":"Applications of Michael addition reaction in organic synthesis","volume":"14","author":"Huang","year":"2017","journal-title":"Curr. Org. Synth."},{"key":"10.1016\/j.jmgm.2024.108911_bib41","doi-asserted-by":"crossref","first-page":"15843","DOI":"10.1002\/chem.202003392","article-title":"Lewis acid promoted dearomatization of naphthols","volume":"26","author":"Kulish","year":"2020","journal-title":"Chem. Eur J."},{"key":"10.1016\/j.jmgm.2024.108911_bib42","doi-asserted-by":"crossref","first-page":"14078","DOI":"10.1039\/C9CC07172E","article-title":"Acid-catalyzed synthesis of condensed polycyclic diaryl ethers from arenols","volume":"55","author":"Tanii","year":"2019","journal-title":"Chem. Commun."},{"key":"10.1016\/j.jmgm.2024.108911_bib43","doi-asserted-by":"crossref","first-page":"2163","DOI":"10.1021\/ja01302a022","article-title":"The action of bromine in methyl alcoholic solution on phenanthrene; a new route to 9-phenanthrol and 9-phenanthrylamines","volume":"58","author":"Fieser","year":"1936","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.jmgm.2024.108911_bib44","doi-asserted-by":"crossref","first-page":"684","DOI":"10.1246\/nikkashi.1987.684","article-title":"Reaction of carbonyl group of anthraquinone, anthrone, with amine and thiol using titanium(IV) chloride catalyst","volume":"4","author":"Tamano","year":"1987","journal-title":"Nippon Kagaku Kaishi"},{"key":"10.1016\/j.jmgm.2024.108911_bib45","doi-asserted-by":"crossref","first-page":"622","DOI":"10.1080\/10406638.2018.1466812","article-title":"Antibacterial and insecticidal activities of the revived azoanthrols","volume":"40","author":"Dardeer","year":"2020","journal-title":"Polycycl. Aromat. Comp."},{"key":"10.1016\/j.jmgm.2024.108911_bib46","doi-asserted-by":"crossref","first-page":"1711","DOI":"10.1021\/ol025760o","article-title":"Synergistic catalysis of anthrone Dels-Ader reactions","volume":"4","author":"Harrison","year":"2002","journal-title":"Org. Lett."}],"container-title":["Journal of Molecular Graphics and Modelling"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S1093326324002110?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S1093326324002110?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,2,12]],"date-time":"2025-02-12T08:56:16Z","timestamp":1739350576000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S1093326324002110"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3]]},"references-count":45,"alternative-id":["S1093326324002110"],"URL":"https:\/\/doi.org\/10.1016\/j.jmgm.2024.108911","relation":{},"ISSN":["1093-3263"],"issn-type":[{"value":"1093-3263","type":"print"}],"subject":[],"published":{"date-parts":[[2025,3]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Keto-enol Tautomerism of hydroxy-substituted arenes: Theoretical study and experimental consequences","name":"articletitle","label":"Article Title"},{"value":"Journal of Molecular Graphics and Modelling","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.jmgm.2024.108911","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2024 Elsevier Inc. All rights are reserved, including those for text and data mining, AI training, and similar technologies.","name":"copyright","label":"Copyright"}],"article-number":"108911"}}