About: Regio- and Stereocontrolled Synthesis of Oligostilbenoids: Theoretical Highlights at the Supramolecular Level

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Oligostilbenoids (e g, ampelopsin F, viniferin, pallidol) result from homogeneous or heterogeneous coupling of monomeric stilbenoid units, leading to various chemical structures Oligostilbenoid synthesis is regio- and stereocontrolled. To tackle this regio- and stereocontrol, a supramolecular chemistry approach is required that can be achieved by quantum chemistry. The stability of noncovalent pi-stacks, formed between two stilbenoid units prior to oxidation, is accurately evaluated with density functional theory (DFT) including dispersive effects (within the DFT-D formalism). These noncovalent arrangements drive the regiocontrol. The rest of the chemical pathway is a succession of dearomatization and rearomatization stages. The thermodynamics and kinetics of the processes are calculated with classical hybrid functionals. This study allows discrimination between the two main possible chemical pathways, namely, radical-neutral and radical-radical reactions. The former appears more likely, thermodynamics and kinetics being in perfect agreement with the experimental 1:2 ratio obtained for ampelopsin F:pallidol analogues, respectively. Oligostilbenoids (e g, ampelopsin F, viniferin, pallidol) result from homogeneous or heterogeneous coupling of monomeric stilbenoid units, leading to various chemical structures Oligostilbenoid synthesis is regio- and stereocontrolled. To tackle this regio- and stereocontrol, a supramolecular chemistry approach is required that can be achieved by quantum chemistry. The stability of noncovalent pi-stacks, formed between two stilbenoid units prior to oxidation, is accurately evaluated with density functional theory (DFT) including dispersive effects (within the DFT-D formalism). These noncovalent arrangements drive the regiocontrol. The rest of the chemical pathway is a succession of dearomatization and rearomatization stages. The thermodynamics and kinetics of the processes are calculated with classical hybrid functionals. This study allows discrimination between the two main possible chemical pathways, namely, radical-neutral and radical-radical reactions. The former appears more likely, thermodynamics and kinetics being in perfect agreement with the experimental 1:2 ratio obtained for ampelopsin F:pallidol analogues, respectively. (en)
Title	Regio- and Stereocontrolled Synthesis of Oligostilbenoids: Theoretical Highlights at the Supramolecular Level Regio- and Stereocontrolled Synthesis of Oligostilbenoids: Theoretical Highlights at the Supramolecular Level (en)
skos:prefLabel	Regio- and Stereocontrolled Synthesis of Oligostilbenoids: Theoretical Highlights at the Supramolecular Level Regio- and Stereocontrolled Synthesis of Oligostilbenoids: Theoretical Highlights at the Supramolecular Level (en)
skos:notation	RIV/61989592:15310/13:33148618!RIV14-MSM-15310___
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(ED2.1.00/03.0058)
http://linked.open...iv/cisloPeriodika	4
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Trouillas, Patrick
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Palackého v Olomouci / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	101963
http://linked.open...ai/riv/idVysledku	RIV/61989592:15310/13:33148618
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	analogs; oligomers; molecules; complexes; antioxidants; solvent; phenols; resveratrol; stem bark; vatica-rassak (en)
http://linked.open.../riv/klicoveSlovo	phenols oligomers analogs antioxidants complexes molecules solvent stem bark vatica-rassak resveratrol
http://linked.open...odStatuVydavatele	NL - Nizozemsko
http://linked.open...ontrolniKodProRIV	[953C76F0C218]
http://linked.open...i/riv/nazevZdroje	Journal of Natural Products
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Regional Centre of Advanced Technologies and Materials
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	76
http://linked.open...iv/tvurceVysledku	Trouillas, Patrick Di Meo, Florent Sancho-Garcia, Juan C Weber, Jean-Frederic F Velu, Saraswati S
http://linked.open...ain/vavai/riv/wos	000318264700009
issn	0163-3864
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/np300705p
http://localhost/t...ganizacniJednotka	15310

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