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

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Publikace nespadá pod Ekonomicko-správní fakultu, ale pod Středoevropský technologický institut. Oficiální stránka publikace je na webu muni.cz.
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KADAM Shivaji Sambhaji TOUŠEK Jaromír MAIER Lukáš PIPÍŠKA Matej SKLENÁŘ Vladimír MAREK Radek

Rok publikování 2012
Druh Článek v odborném periodiku
Časopis / Zdroj Journal of Molecular Structure
Fakulta / Pracoviště MU

Středoevropský technologický institut

Citace
www http://dx.doi.org/10.1016/j.molstruc.2012.06.034
Doi http://dx.doi.org/10.1016/j.molstruc.2012.06.034
Obor Fyzikální chemie a teoretická chemie
Klíčová slova Density-functional theory; Nuclear magnetic shielding; Conformational analysis; Nucleus-independent chemical shift; Localized molecular orbitals; Berberine
Přiložené soubory
Popis 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).
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