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In particular, for the first time, <jats:bold>Ct<\/jats:bold> and not the flavylium cation is reported as the most stable species in mixtures containing water at pH 1.0. The rate of <jats:bold>Ct<\/jats:bold> formation as a function of the water content exhibits a bell\u2010shaped dependence, showing a maximum at approximately 50\u2009% water. These trends are explained by a slower <jats:italic>cis<\/jats:italic>\u2013<jats:italic>trans<\/jats:italic> isomerization in ethanol relative to that in water due to the expected stabilization in polar solvents of the zwitterionic intermediate; on the other hand, the decrease in the concentration of <jats:italic>cis<\/jats:italic>\u2010chalcone (<jats:bold>Cc<\/jats:bold>) in the pseudoequilibrium with increasing water content, gives rise to a decrease in the rate of <jats:bold>Ct<\/jats:bold> formation (<jats:italic>k<\/jats:italic><jats:sub>obs<\/jats:sub>=<jats:italic>k<\/jats:italic><jats:sub>real<\/jats:sub>[<jats:bold>Cc<\/jats:bold>]). The hydration reaction was found to be much more efficient when water is present in low concentrations. This result has important consequences for the interpretation of the coloring phenomena caused by anthocyanins in plants, as well as for applications of flavylium compounds in the field of optical memories.<\/jats:p>","DOI":"10.1002\/chem.200600020","type":"journal-article","created":{"date-parts":[[2006,8,22]],"date-time":"2006-08-22T16:25:04Z","timestamp":1156263904000},"page":"7906-7912","source":"Crossref","is-referenced-by-count":13,"title":["Solvent Effects on the Thermal and Photochemical Reactions of 4\u2032\u2010Iodo\u20108\u2010methoxyflavylium and Their Consequences on the Coloring Phenomena Caused by Anthocyanins in Plants"],"prefix":"10.1002","volume":"12","author":[{"given":"Raquel","family":"Gomes","sequence":"first","affiliation":[]},{"given":"A. 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