About: Oxygen Superbases as Polar Binding Pockets in Nonpolar Solvents

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	A novel class of chiral superbases derived from the 2,2 '-bipyridyl-N,N-dioxide skeleton are presented. Combined experimental and theoretical data reveal that their proton affinities are on the order of 1050 kJ mol(-1), with protonation occurring at the oxygen atoms in a chelating manner. In the free bases, the oxygen atoms form a strongly polar binding site hidden in a hydrophobic envelope formed by the hydrocarbon backbone of the superbases. This chiral molecular structure can entrap polar intermediates or polarized transition structures and stabilize them in nonpolar solvents. Specifically, this mode of catalysis is shown for the coupling of benzaldehyde and allyltrichlorosilane. A novel class of chiral superbases derived from the 2,2 '-bipyridyl-N,N-dioxide skeleton are presented. Combined experimental and theoretical data reveal that their proton affinities are on the order of 1050 kJ mol(-1), with protonation occurring at the oxygen atoms in a chelating manner. In the free bases, the oxygen atoms form a strongly polar binding site hidden in a hydrophobic envelope formed by the hydrocarbon backbone of the superbases. This chiral molecular structure can entrap polar intermediates or polarized transition structures and stabilize them in nonpolar solvents. Specifically, this mode of catalysis is shown for the coupling of benzaldehyde and allyltrichlorosilane. (en)
Title	Oxygen Superbases as Polar Binding Pockets in Nonpolar Solvents Oxygen Superbases as Polar Binding Pockets in Nonpolar Solvents (en)
skos:prefLabel	Oxygen Superbases as Polar Binding Pockets in Nonpolar Solvents Oxygen Superbases as Polar Binding Pockets in Nonpolar Solvents (en)
skos:notation	RIV/00216208:11310/10:10062507!RIV11-MSM-11310___
http://linked.open...avai/riv/aktivita	S Z
http://linked.open...avai/riv/aktivity	S, Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika	36
http://linked.open...vai/riv/dodaniDat	2011
http://linked.open...aciTvurceVysledku	Kotora, Martin Kadlčíková, Aneta Roithová, Jana Jašíková, Lucie
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 Karlova v Praze / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	277894
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/10:10062507
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	mass spectrometry; DFT methods; Superbases (en)
http://linked.open.../riv/klicoveSlovo	mass spectrometry DFT methods Superbases
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[8795EE6CB1C7]
http://linked.open...i/riv/nazevZdroje	Journal of the American Chemical Society
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...UplatneniVysledku	2010
http://linked.open...v/svazekPeriodika	132
http://linked.open...iv/tvurceVysledku	Kadlčíková, Aneta Kotora, Martin Roithová, Jana Ducháčková, Lucie
http://linked.open...ain/vavai/riv/wos	000282074200029
http://linked.open...n/vavai/riv/zamer	Nové molekulární systémy pro pokročilé aplikace prospěšné pro zdraví a šetrné k životnímu prostředí
issn	0002-7863
number of pages	8 (xsd:int)
http://localhost/t...ganizacniJednotka	11310
is http://linked.open...avai/riv/vysledek of	Oxygen Superbases as Polar Binding Pockets in Nonpolar Solvents Oxygen Superbases as Polar Binding Pockets in Nonpolar Solvents Oxygen Superbases as Polar Binding Pockets in Nonpolar Solvents

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