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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Bibliographic Details
Published in:	Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 50; no. 3; pp. 336 - 348
Main Authors:	Lebed, A. V., Biryukov, A. V., Mchedlov-Petrossyan, N. O.
Format:	Journal Article
Language:	English
Published:	Boston Springer US 01-06-2014 Springer
Subjects:	Chemistry Chemistry and Materials Science Fluorescein Organic Chemistry Pharmacy Surface active agents fluorescein quantum-chemical calculations tetranitrofluorescein aminofluorescein eosin tautomerism of ions and molecules in solutions
Online Access:	Get full text
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Summary:	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