ArticleMolecules (Basel, Switzerland)2024
Stationary External Electric Field-Mimicking the Solvent Effect on the Ground-State Tautomerism and Excited-State Proton Transfer in 8-(Benzo[d]thiazol-2-yl)quinolin-7-ol.
Article in Molecules (Basel, Switzerland), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Kinetics of Proton Transfer and String of Conformational Transformation for 4-Pyridone-3-carboxylic Acid Under External Electric Field.Molecules (Basel, Switzerland) · 2025Article
- Improving the Long-Range Intramolecular Proton Transfer-Further Molecular Design of the Successful Molecular Switch 8-(Benzo[d]thiazol-2-yl)quinolin-7-ol (HQBT).Molecules (Basel, Switzerland) · 2025Article
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3 authors.
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Abstract
The effect of the external electric field on the ground-state tautomerism in 8-(benzo[d]thiazol-2-yl)quinolin-7-ol has been studied by using density functional theory. The compound exists as an enol tautomer (off state) and under the influence of the external electric field a long-range intramolecular proton transfer can occur, placing the tautomeric proton at the quinolyl nitrogen atom (on state). This is a result of the much higher dipole moment of the end keto tautomer and indicates that the external electric field can be used to mimic the implicit solvent effect in tautomeric systems. In the excited state, the further stabilization of the most polar on state leads to a situation when the excited-state intramolecular proton transfer becomes impossible, limiting the intramolecular rotation to the conical intersection region.
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