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

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Authors

KADAM Shivaji Sambhaji TOUŠEK Jaromír MAIER Lukáš PIPÍŠKA Matej SKLENÁŘ Vladimír MAREK Radek

Year of publication 2012
Type Article in Periodical
Magazine / Source Journal of Molecular Structure
MU Faculty or unit

Central European Institute of Technology

Citation
Web http://dx.doi.org/10.1016/j.molstruc.2012.06.034
Doi http://dx.doi.org/10.1016/j.molstruc.2012.06.034
Field Physical chemistry and theoretical chemistry
Keywords Density-functional theory; Nuclear magnetic shielding; Conformational analysis; Nucleus-independent chemical shift; Localized molecular orbitals; Berberine
Attached files
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).
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