A Quantum-Chemical Study of Tautomeric Equilibria of Fluorescein Dyes in DMSO

A Quantum-Chemical Study of Tautomeric Equilibria of Fluorescein Dyes in DMSO

We evaluated the relative thermodynamic stability of various molecular and anionic tautomers of fluorescein, its 2,4,5,7-tetrabromo derivative (eosin), and also sulfofluorescein, 4'- and 5'-amino-fluoresceins, and 2,4,5,7-tetranitrofluorescein in DMSO, based on a quantum-chemical investiga...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2014-06, Vol.50 (3), p.336-348
Hauptverfasser: Lebed, A. V., Biryukov, A. V., Mchedlov-Petrossyan, N. O.
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry and Materials Science
Fluorescein
Organic Chemistry
Pharmacy
Surface active agents
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Zusammenfassung:We evaluated the relative thermodynamic stability of various molecular and anionic tautomers of fluorescein, its 2,4,5,7-tetrabromo derivative (eosin), and also sulfofluorescein, 4'- and 5'-amino-fluoresceins, and 2,4,5,7-tetranitrofluorescein in DMSO, based on a quantum-chemical investigation; in some cases the calculations were performed for gas phase and aqueous solutions. These results, obtained for 39 structures (15 of which were studied by quantum-chemical methods for the first time) generally agree with the previously published experimental data.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-014-1481-8