About: 13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Tropane, tropinone, pseudopelletierine and cocaine were oxidized in situ in a nuclear magnetic resonance (NMR) tube providing mixtures of exo/endo N-oxides. Observed 13C chemical shifts were correlated with values calculated by gauge-including atomic orbitals density functional theory (DFT) OPBE/6-31G method using DFT B3LYP/6-31G optimized geometries. The same method of 13C chemical shift calculation was applied on series of methyl-substituted 1-methylpiperidines and their epimeric N-oxides described in literature. The results show that using this undemanding calculation method enables assignment of configuration of NO group in N-epimeric saturated heterocyclic N-oxides. The approach enables assigning of the configuration with high degree of certainty even if NMR data of only one isomer are available. An improved method of in situ oxidation of starting amines in an NMR tube is also described. Tropane, tropinone, pseudopelletierine and cocaine were oxidized in situ in a nuclear magnetic resonance (NMR) tube providing mixtures of exo/endo N-oxides. Observed 13C chemical shifts were correlated with values calculated by gauge-including atomic orbitals density functional theory (DFT) OPBE/6-31G method using DFT B3LYP/6-31G optimized geometries. The same method of 13C chemical shift calculation was applied on series of methyl-substituted 1-methylpiperidines and their epimeric N-oxides described in literature. The results show that using this undemanding calculation method enables assignment of configuration of NO group in N-epimeric saturated heterocyclic N-oxides. The approach enables assigning of the configuration with high degree of certainty even if NMR data of only one isomer are available. An improved method of in situ oxidation of starting amines in an NMR tube is also described. (en)
Title	13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides 13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides (en)
skos:prefLabel	13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides 13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides (en)
skos:notation	RIV/61388963:_____/12:00378932!RIV13-AV0-61388963
http://linked.open...avai/predkladatel	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/09/1919), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	6
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Buděšínský, Miloš Dračínský, Martin Pohl, Radek Slavětínská, Lenka Vaněk, Václav
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	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	183265
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/12:00378932
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	NMR; 13C; 1H; saturated heterocyclic N-oxides; chemical shift calculations; DFT (en)
http://linked.open.../riv/klicoveSlovo	chemical shift calculations saturated heterocyclic N-oxides NMR DFT 13C 1H
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[A38A7DC40B5D]
http://linked.open...i/riv/nazevZdroje	Magnetic Resonance in Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Development of methods for configuration determination at chiral sulfur, nitrogen or phosphorus atom using NMR spectroscopy and ab initio calculations
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	50
http://linked.open...iv/tvurceVysledku	Buděšínský, Miloš Dračínský, Martin Pohl, Radek Slavětínská, Lenka Vaněk, Václav Potmischil, F.
http://linked.open...ain/vavai/riv/wos	000304086100002
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	0749-1581
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/mrc.3810
is http://linked.open...avai/riv/vysledek of	13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides

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