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The hydrogen\u2010bonding network involving the enolate thiazole moiety is stronger than that of the benzothiazole phenolate moiety. Therefore, enolate oxyluciferin should be stabilized versus the phenolate anion. This difference in strength is attributed to the fact that the thiazole moiety has more potential hydrogen\u2010bond acceptors near the proton donor atom than the benzothiazole moiety. Moreover, the phenol\u2010based excited\u2010state proton transfer leads to a decrease in the hydrogen\u2010bond acceptor potential of the thiazole atoms. The ground\u2010state enol\u2010based acidity of oxyluciferin is also studied. This phenomenon can be explained by stabilization of the enolate anion through strengthening of a bond between water and the nitrogen atom of the thiazole ring, in an enol\u2010based proton\u2010transfer\u2010dependent way.<\/jats:p>","DOI":"10.1002\/cphc.201402533","type":"journal-article","created":{"date-parts":[[2014,11,17]],"date-time":"2014-11-17T15:58:06Z","timestamp":1416239886000},"page":"455-464","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Theoretical Study of the Nontraditional Enol\u2010Based Photoacidity of Firefly Oxyluciferin"],"prefix":"10.1002","volume":"16","author":[{"given":"Lu\u00eds","family":"Pinto da Silva","sequence":"first","affiliation":[]},{"given":"Joaquim C. 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