Ground-State Tautomerism and Excited-State Proton Transfer in 7-Hydroxy-4-methyl-8-((phenylimino)methyl)-2H-chromen-2-one as a Potential Proton Crane

The tautomerism in the title compound as a potential long-range proton transfer (PT) switch has been studied by using the DFT and TD-DFT approaches. The data show that in aprotic solvents, the enol tautomer dominates, while the increase in the content of the keto tautomer (short-range PT) rises as a...

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Bibliographic Details
Published in:Physchem 2024-03, Vol.4 (1), p.91-105
Main Authors: Nedeltcheva-Antonova, Daniela, Antonov, Liudmil
Format: Article
Language:English
Subjects:
7-hydroxy-3-methylcoumarin
7-hydroxy-coumarin
Cranes & hoists
DFT
Protons
Schiff base
Solvents
tautomerism
TD-DFT
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Summary:The tautomerism in the title compound as a potential long-range proton transfer (PT) switch has been studied by using the DFT and TD-DFT approaches. The data show that in aprotic solvents, the enol tautomer dominates, while the increase in the content of the keto tautomer (short-range PT) rises as a function of polarity of the solvent. In ethanol, due to specific solute–solvent stabilization through intermolecular hydrogen bonding, a substantial amount of the keto forms exists in solution. The irradiation leads to two competitive processes in the excited state, namely ESIPT and trans/cis isomerization around the azomethine bond as in other structurally similar Schiff bases. The studied compound is not suitable for bistable tautomeric switching, where long-range PT occurs, due to the difficult enolization of the coumarin carbonyl group.
ISSN:2673-7167
2673-7167
DOI:10.3390/physchem4010007