About: Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts

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About: Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1016/j.tet.2014.04.047
Description	The six-membered saturated heterocycles-4-tert-butyl-1 -methylpiperidine, 4-tert-butyl-1methylphosphine, 4-tert-butyl-tetrahydro-2H-thiopyran, and 4-tert-butyl-tetrahydro-2H-selenopyran were prepared as suitable model compounds with well-defined geometry for an NMR study of their oxidation products. The corresponding epimeric N-oxides, phosphinoxides, sulfoxides, and selenoxides were obtained by standard chemical preparation and also by in situ oxidation with meta-chloroperbenzoic acid directly in the NMR tube. The experimental H-1 and C-13 chemical shifts were compared with corresponding calculated data obtained by CIAO approach with DFT, MP2, and HF methods and various basis sets. The correlation of experimental versus calculated data showed the possibility to determine the stereochemistiy of the epimeric oxidation products using fast DFT B3LYP/6-31G* method for both geometry optimization and NMR chemical shifts calculation. The six-membered saturated heterocycles-4-tert-butyl-1 -methylpiperidine, 4-tert-butyl-1methylphosphine, 4-tert-butyl-tetrahydro-2H-thiopyran, and 4-tert-butyl-tetrahydro-2H-selenopyran were prepared as suitable model compounds with well-defined geometry for an NMR study of their oxidation products. The corresponding epimeric N-oxides, phosphinoxides, sulfoxides, and selenoxides were obtained by standard chemical preparation and also by in situ oxidation with meta-chloroperbenzoic acid directly in the NMR tube. The experimental H-1 and C-13 chemical shifts were compared with corresponding calculated data obtained by CIAO approach with DFT, MP2, and HF methods and various basis sets. The correlation of experimental versus calculated data showed the possibility to determine the stereochemistiy of the epimeric oxidation products using fast DFT B3LYP/6-31G* method for both geometry optimization and NMR chemical shifts calculation. (en)
Title	Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts (en)
skos:prefLabel	Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts Determination of the configuration in six-membered saturated heterocycles (N, P, S, Se) and their oxidation products using experimental and calculated NMR chemical shifts (en)
skos:notation	RIV/00216208:11310/14:10272022!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(GA13-24880S), P(GA203/09/1919)
http://linked.open...iv/cisloPeriodika	25
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Císařová, Ivana
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	10830
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/14:10272022
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	X-ray structures; quantum chemical calculations; NMR; configuration; oxidation products; Se); S; P; six-membered saturated heterocycles (N (en)
http://linked.open.../riv/klicoveSlovo	P NMR quantum chemical calculations oxidation products configuration S X-ray structures Se) six-membered saturated heterocycles (N
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[841BD2A56ABE]
http://linked.open...i/riv/nazevZdroje	Tetrahedron
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...vavai/riv/projekt	Struktura a vlastnosti modifikovaných složek nukleových kyselin Development of methods for configuration determination at chiral sulfur, nitrogen or phosphorus atom using NMR spectroscopy and ab initio calculations
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	70
http://linked.open...iv/tvurceVysledku	Císařová, Ivana Dračínský, Martin Pohl, Radek Sychrovský, Vladimír Vaněk, Václav Pícha, Jan Budešínský, Miloš Poštová-Slavětínská, Lenka
http://linked.open...ain/vavai/riv/wos	000336699900006
issn	0040-4020
number of pages	16 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.tet.2014.04.047
http://localhost/t...ganizacniJednotka	11310

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