About: Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis

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About: Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis 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.molstruc.2012.06.034
Description	We report here the preparation and the structural investigation into a series of 8-(indol-1-yl)-7,8-dihydroprotoberberine derivatives derived from berberine, palmatine, and coptisine. Structures of these new compounds were characterized mainly by 2D NMR spectroscopy and the conformational behavior was investigated by using methods of density-functional theory (DFT). PBE0/6-311+G calculated NMR chemical shifts for selected derivatives correlate excellently with the experimental NMR data and support the structural conclusions drawn from the NMR experiments. An interesting role of the nitrogen atom in position N7' of the indole moiety in 8-(7-azaindol-1-yl)-7,8-dihydroprotoberberines as compared to other 8-indolyl derivatives is investigated in detail. The experimentally observed trends in NMR chemical shifts are rationalized by DFT calculations and analysis based on the nucleus-independent chemical shifts (NICS) and natural localized molecular orbitals (NLMOs). We report here the preparation and the structural investigation into a series of 8-(indol-1-yl)-7,8-dihydroprotoberberine derivatives derived from berberine, palmatine, and coptisine. Structures of these new compounds were characterized mainly by 2D NMR spectroscopy and the conformational behavior was investigated by using methods of density-functional theory (DFT). PBE0/6-311+G calculated NMR chemical shifts for selected derivatives correlate excellently with the experimental NMR data and support the structural conclusions drawn from the NMR experiments. An interesting role of the nitrogen atom in position N7' of the indole moiety in 8-(7-azaindol-1-yl)-7,8-dihydroprotoberberines as compared to other 8-indolyl derivatives is investigated in detail. The experimentally observed trends in NMR chemical shifts are rationalized by DFT calculations and analysis based on the nucleus-independent chemical shifts (NICS) and natural localized molecular orbitals (NLMOs). (en)
Title	Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis (en)
skos:prefLabel	Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis (en)
skos:notation	RIV/00216224:14740/12:00060457!RIV13-MSM-14740___
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(ED1.1.00/02.0068)
http://linked.open...iv/cisloPeriodika	Nov
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Toušek, Jaromír Maier, Lukáš Sklenář, Vladimír Pipíška, Matej Marek, Radek Kadam, Shivaji Sambhaji
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	Masarykova univerzita / Středoevropský technologický institut
http://linked.open...dnocenehoVysledku	175946
http://linked.open...ai/riv/idVysledku	RIV/00216224:14740/12:00060457
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Density-functional theory; Nuclear magnetic shielding; Conformational analysis; Nucleus-independent chemical shift; Localized molecular orbitals; Berberine (en)
http://linked.open.../riv/klicoveSlovo	Conformational analysis Nuclear magnetic shielding Berberine Density-functional theory Localized molecular orbitals Nucleus-independent chemical shift
http://linked.open...odStatuVydavatele	NL - Nizozemsko
http://linked.open...ontrolniKodProRIV	[A2CAA2AA3CB2]
http://linked.open...i/riv/nazevZdroje	Journal of Molecular Structure
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	6 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Central european institute of technology
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	1028
http://linked.open...iv/tvurceVysledku	Marek, Radek Pipíška, Matej Sklenář, Vladimír Kadam, Shivaji Sambhaji Maier, Lukáš Toušek, Jaromír
http://linked.open...ain/vavai/riv/wos	000311174800006
issn	0022-2860
number of pages	8 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.molstruc.2012.06.034
http://localhost/t...ganizacniJednotka	14740

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