Keto‐enol tautomerism from the electron delocalization perspective
Sign Up to like & getrecommendations! Published in 2022 at "Journal of Computational Chemistry"
DOI: 10.1002/jcc.26858
Abstract: The equilibrium between keto and enol forms in acetylacetone and its derivatives is studied using electron delocalization indices and delocalization tensor density. We demonstrate how electron delocalization governs the equilibrium between keto and enol forms.… read more here.
Keywords: keto enol; stable enols; delocalization; electron delocalization ... See more keywords
Natural polyprenylated benzophenone: keto-enol tautomerism from density functional calculations and the AIM theory
Sign Up to like & getrecommendations! Published in 2017 at "Journal of Molecular Modeling"
DOI: 10.1007/s00894-017-3251-x
Abstract: The quantum theory of atoms in molecules (QTAIM) and density functional theory (DFT) calculations were employed to investigate the structure and tautomeric equilibrium of epiclusianone, a polyisoprenylated benzophenone with interesting biological activities. Two different exchange-correlation… read more here.
Keywords: density functional; keto enol; density; polyprenylated benzophenone ... See more keywords
Keto‐enol‐based modification on piperlongumine to generate a potent Cu(II) ionophore that triggers redox imbalance and death of HepG2 cells
Sign Up to like & getrecommendations! Published in 2018 at "Free Radical Biology and Medicine"
DOI: 10.1016/j.freeradbiomed.2018.03.029
Abstract: ABSTRACT Altered redox status including higher levels of copper in cancer cells than in normal cells inspired many researchers to develop copper ionophores targeting this status. We have recently found that flavon‐3‐ol (3‐HF) works as… read more here.
Keywords: keto enol; piperlongumine; hepg2 cells; death ... See more keywords
Regioselective Synthesis of 6-Chlorofulvene and 6-Aminofulvene via Keto–Enol Tautomerism
Sign Up to like & getrecommendations! Published in 2020 at "Journal of Chemical Education"
DOI: 10.1021/acs.jchemed.0c00039
Abstract: Keto–enol tautomerism is a special example of structural isomerism. In this experiment, 6-chlorofulvene is predominantly yielded during the chlorination reaction of 6′-hydroxyfulvene with POCl3 in ... read more here.
Keywords: keto enol; regioselective synthesis; chlorofulvene; enol tautomerism ... See more keywords
Photoswitchable Keto-Enol Tautomerism Driven by Light-Induced Change in Antiaromaticity.
Sign Up to like & getrecommendations! Published in 2022 at "Organic letters"
DOI: 10.1021/acs.orglett.2c03441
Abstract: The bidirectional interconversion between ketone and enol structures of 4-cyclopentene-1,3-dione derivatives was realized by photoswitching of fused dithienylethene using UV and visible light. A loss of antiaromaticity offered the driving force for light-triggered enolization and… read more here.
Keywords: light induced; enol tautomerism; enol; photoswitchable keto ... See more keywords
Role of Keto–Enol Tautomerization in the Copper-Catalyzed Hydrogenation of Ketones
Sign Up to like & getrecommendations! Published in 2019 at "ACS Catalysis"
DOI: 10.1021/acscatal.9b00279
Abstract: Hydrogenation of alkoxy intermediates is often rate-limiting in the hydrogenation of carbonyl groups over copper catalysts. Using first-principles microkinetic simulations with coverage-dependent kinetic parameters, we find that an enol hydrogenation pathway, that is, not passing… read more here.
Keywords: keto enol; copper; tautomerization copper; role keto ... See more keywords
Theoretical Study on the Epimerization of Azlactone Rings: Keto–Enol Tautomerism or Base-Mediated Racemization?
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DOI: 10.1021/acsomega.8b00060
Abstract: Azlactones are versatile heterocycles employed in a diversity of transformations; the main drawback of these cycles consists in the epimerization of the α-carbonyl stereocenter during its preparation. We hereby present a theoretical study to explain… read more here.
Keywords: tautomerism base; theoretical study; racemization; keto enol ... See more keywords
Novel keto-enol tautomerism in 1,3,5-trihydroxybenzene systems.
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DOI: 10.1039/d0cc03639k
Abstract: We report a new synthesis of the water-soluble compound 1,3,5-trihydroxy-2,4,6-trimethylsulfonic acid (1), which exists in two tautomeric forms (60 : 40::enol%:keto%) and can be used as a proton conductor. Quantum chemical calculations show the importance of intramolecular… read more here.
Keywords: novel keto; keto enol; keto; tautomerism trihydroxybenzene ... See more keywords
Cascade aryne insertion/vinylogous aldol reaction of vinyl-substituted β-keto/enol carbonyls.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d1cc06810e
Abstract: Cyclic and acyclic vinyl substituted β-keto/enol carbonyl substrates, on reaction with arynes, result in differentially substituted naphthyl carbocycles, hitherto difficult to synthesize with existing protocols. While the substitutions on the arynes have no role, the… read more here.
Keywords: keto enol; vinyl substituted; keto; substituted keto ... See more keywords
The keto–enol equilibrium and thermal conversion kinetics of 2- and 4-hydroxyacetophenone in the gas phase: a DFT study
Sign Up to like & getrecommendations! Published in 2018 at "Molecular Physics"
DOI: 10.1080/00268976.2017.1374483
Abstract: ABSTRACT Keto–enol tautomeric equilibrium and the mechanism of thermal conversion of 2- and 4-hydroxyacetophenone in gas phase have been studied by means of electronic structure calculations using density functional theory (DFT). A topological analysis of… read more here.
Keywords: mechanism; keto enol; hydroxyacetophenone gas; thermal conversion ... See more keywords
The Keto–Enol Tautomerism of Biliverdin in Bacteriophytochrome: Could it Explain the Bathochromic Shift in the Pfr Form?†
Sign Up to like & getrecommendations! Published in 2020 at "Photochemistry and Photobiology"
DOI: 10.1111/php.13341
Abstract: Phytochromes are ubiquitous photoreceptors found in plants, eukaryotic algae, bacteria and fungi. Particularly, when bacteriophytochrome is irradiated with light, a Z‐to‐E (photo)isomerization takes place in the biliverdin chromophore as part of the Pr‐to‐Pfr conversion. This… read more here.
Keywords: keto enol; bathochromic shift; keto; reaction ... See more keywords