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The stability, relative energy of each of chemical species (thermodynamics), and their rates of interconversion (kinetics) are very dependent on these substituents. By comparing the mole fraction distribution at equilibrium of the three multistate systems with the parent 3\u2032,4\u2032,7\u2010trihydroxyflavylium, introduction of a methyl substituent in position 3 increases the mole fraction of hemiketal at the expense of the <jats:italic>trans<\/jats:italic>\u2010chalcone and increases the hydration rate very significantly; a hydroxyl substituent in position 3 gives rise to a degradation process, as observed in anthocyanidins. In the case of 3\u2010chloro\u20103\u2032,4\u2032,7\u2010trihydroxyflavylium, a dramatic increase of the flavylium cation acidity was observed and a photochromic system can be operated upon irradiation of the respective <jats:italic>trans<\/jats:italic>\u2010chalcone in 1\u2009<jats:sc>m<\/jats:sc> HCl. According to the photochromic response of 3,3\u2032,4\u2032,7\u2010tetrahydroxyflavylium and 3\u2032,4\u2032,7\u2010trihydroxyflavylium, some requirements for a good photochromic performance are discussed.<\/jats:p>","DOI":"10.1002\/chem.201601564","type":"journal-article","created":{"date-parts":[[2016,7,28]],"date-time":"2016-07-28T03:08:04Z","timestamp":1469675284000},"page":"12495-12505","source":"Crossref","is-referenced-by-count":11,"title":["Effect of Methyl, Hydroxyl, and Chloro Substituents in Position 3 of 3\u2032,4\u2032,7\u2010Trihydroxyflavylium: Stability, Kinetics, and Thermodynamics"],"prefix":"10.1002","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8691-4628","authenticated-orcid":false,"given":"Alfonso","family":"Alejo\u2010Armijo","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Inorg\u00e1nica y Org\u00e1nica Facultad de Ciencias Experimentales Universidad de Ja\u00e9n  23071 Ja\u00e9n Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2319-7873","authenticated-orcid":false,"given":"Sof\u00eda","family":"Salido","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Inorg\u00e1nica y Org\u00e1nica Facultad de Ciencias Experimentales Universidad de Ja\u00e9n  23071 Ja\u00e9n Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5532-8535","authenticated-orcid":false,"given":"Joaqu\u00edn","family":"Altarejos","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Inorg\u00e1nica y Org\u00e1nica Facultad de Ciencias Experimentales Universidad de Ja\u00e9n  23071 Ja\u00e9n Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1333-9076","authenticated-orcid":false,"given":"A. 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