{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,7]],"date-time":"2026-02-07T18:42:53Z","timestamp":1770489773822,"version":"3.49.0"},"reference-count":46,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2018,11,13]],"date-time":"2018-11-13T00:00:00Z","timestamp":1542067200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/QUI\/00081\/2013"],"award-info":[{"award-number":["UID\/QUI\/00081\/2013"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["SFRH\/BPD\/78552\/2011"],"award-info":[{"award-number":["SFRH\/BPD\/78552\/2011"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Operational Programme for Competitiveness and Internationalisation, COMPETE","award":["POCI-01-0145-FEDER-006980"],"award-info":[{"award-number":["POCI-01-0145-FEDER-006980"]}]},{"name":"CCRN - Comiss\u00e3o de Coordena\u00e7\u00e3o da Regi\u00e3o Norte","award":["NORTE-01-0145-FEDER-000028"],"award-info":[{"award-number":["NORTE-01-0145-FEDER-000028"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The present work addresses computational research focused on the energetic and structural properties of four isomers monohydroxyxanthone, using the G3(MP2)\/\/B3LYP method, in order to evaluate the influence of the hydroxyl (\u2014OH moiety) functional group on the xanthone molecule. The combination of these computational results with previous experimental data of these compounds enabled the determination of their enthalpies, entropies and Gibbs energies of formation, in the gaseous phase, and consequently to infer about the relative thermodynamic stability of the four isomers. Other issues were also addressed for the hydroxyxanthone isomers, namely the conformational and the tautomeric equilibrium analysis of the optimized molecular structures, the frontier orbitals, and the electrostatic potential energy maps. Complementarily, an energetic study of the intramolecular     O \u2014 H \u22ef O     hydrogen bond for 1-hydroxanthone was also performed.<\/jats:p>","DOI":"10.3390\/molecules23112962","type":"journal-article","created":{"date-parts":[[2018,11,14]],"date-time":"2018-11-14T02:42:41Z","timestamp":1542163361000},"page":"2962","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Influence of Hydroxyl Functional Group on the Structure and Stability of Xanthone: A Computational Approach"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3670-2595","authenticated-orcid":false,"given":"Vera L. S.","family":"Freitas","sequence":"first","affiliation":[{"name":"Centro de Investiga\u00e7\u00e3o em Qu\u00edmica da Universidade do Porto (CIQUP), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, P-4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0482-0308","authenticated-orcid":false,"given":"Maria D. M. C.","family":"Ribeiro da Silva","sequence":"additional","affiliation":[{"name":"Centro de Investiga\u00e7\u00e3o em Qu\u00edmica da Universidade do Porto (CIQUP), Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, P-4169-007 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2018,11,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2613","DOI":"10.1002\/hlca.19740570838","article-title":"Synthesis of new xanthones, I","volume":"57","author":"Pinto","year":"1974","journal-title":"Helv. Chim. 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