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Open AccessArticle

Tautomerism in Azo and Azomethyne Dyes: When and If Theory Meets Experiment

Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia 1113, Bulgaria
Molecules 2019, 24(12), 2252; https://doi.org/10.3390/molecules24122252
Received: 3 June 2019 / Revised: 13 June 2019 / Accepted: 14 June 2019 / Published: 17 June 2019
(This article belongs to the Special Issue Tautomerism and Proton Transfer Related Phenomena)
The performance of 26 hybrid density functionals was tested against a tautomeric dataset (TautData), containing experimental information for the keto-enol tautomeric equilibrium in 16 tautomeric azodyes and Schiff bases in cyclohexane, carbon tetrachloride and acetonitrile. The results have shown that MN12-SX, BHandH and M06-2X can be used to describe the tautomeric state of the core structures in the frame of ~0.5 kcal/mol error and correctly predict the tautomeric state in respect of dominating tautomeric form. Among them MN12-SX is the best performer, although it fails to describe the nonplanarity of some of the enol tautomers. The same experimental dataset was used to develop and test a special DFT functional (TautLYP) aimed at describing the tautomeric state in azo- and azomethyne compounds in solution when nonspecific solvents are used. View Full-Text
Keywords: DFT; tautomerism; azonaphthols; Schiff bases; optical spectroscopy; chemometrics DFT; tautomerism; azonaphthols; Schiff bases; optical spectroscopy; chemometrics
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Antonov, L. Tautomerism in Azo and Azomethyne Dyes: When and If Theory Meets Experiment. Molecules 2019, 24, 2252.

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