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The enol form of both compounds shows a strong bathochromic shift of the UV\/Vis absorption band compared to the rarely coloured keto form. The keto\u2013enol equilibria of the five studied dyes are strongly dependent on the properties of the environment as shown by solvatochromic studies in ionic liquids and a set of organic solvents. Enol form development of the barbituric acid dyes is also associated with alteration of the hydrogen bonding pattern from the ADA to the DDA type (A=hydrogen bond acceptor site, D=donor site). Receptor\u2010induced altering of ADA towards DDA hydrogen bonding patterns of the chromophores are utilised to study supramolecular complex formation. As complementary receptors 9\u2010ethyladenine, 1\u2010<jats:italic>n<\/jats:italic>\u2010butylcytosine, 1\u2010<jats:italic>n<\/jats:italic>\u2010butylthymine, 9\u2010ethylguanidine and 2,6\u2010diacetamidopiridine were used. The UV\/Vis spectroscopic response of acid\u2013base reaction compared to supramolecular complex formation is evaluated by <jats:sup>1<\/jats:sup>H\u2005NMR titration experiments and X\u2010ray crystal structure analyses. An increased acidity of the barbituric acid derivative promotes genuine salt formation. In contrast, supramolecular complex formation is preferred for the weaker acidic barbituric acid.<\/jats:p>","DOI":"10.1002\/chem.201504932","type":"journal-article","created":{"date-parts":[[2016,3,6]],"date-time":"2016-03-06T02:37:34Z","timestamp":1457231854000},"page":"5734-5748","source":"Crossref","is-referenced-by-count":20,"title":["Interactions of Enolizable Barbiturate Dyes"],"prefix":"10.1002","volume":"22","author":[{"given":"Alexander","family":"Schade","sequence":"first","affiliation":[{"name":"Technische Universit\u00e4t Chemnitz Department of Polymer Chemistry  09107 Chemnitz Germany), Fax: (+49)\u2009371-531-21239"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Katja","family":"Schreiter","sequence":"additional","affiliation":[{"name":"Technische Universit\u00e4t Chemnitz Department of Polymer Chemistry  09107 Chemnitz Germany), Fax: 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