| KADAM, Shivaji Sambhaji, Jaromír TOUŠEK, Lukáš MAIER, Matej PIPÍŠKA, Vladimír SKLENÁŘ a Radek MAREK. Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis. Journal of Molecular Structure. Amsterdam: Elsevier, 2012, roč. 1028, Nov, s. 31-38. ISSN 0022-2860. Dostupné z: https://dx.doi.org/10.1016/j.molstruc.2012.06.034. |
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@article{987470,
author = {Kadam, Shivaji Sambhaji and Toušek, Jaromír and Maier, Lukáš and Pipíška, Matej and Sklenář, Vladimír and Marek, Radek},
article_location = {Amsterdam},
article_number = {Nov},
doi = {http://dx.doi.org/10.1016/j.molstruc.2012.06.034},
keywords = {Density-functional theory; Nuclear magnetic shielding; Conformational analysis; Nucleus-independent chemical shift; Localized molecular orbitals; Berberine},
language = {eng},
issn = {0022-2860},
journal = {Journal of Molecular Structure},
title = {Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis},
url = {http://dx.doi.org/10.1016/j.molstruc.2012.06.034},
volume = {1028},
year = {2012}
}
TY - JOUR
ID - 987470
AU - Kadam, Shivaji Sambhaji - Toušek, Jaromír - Maier, Lukáš - Pipíška, Matej - Sklenář, Vladimír - Marek, Radek
PY - 2012
TI - Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis
JF - Journal of Molecular Structure
VL - 1028
IS - Nov
SP - 31-38
EP - 31-38
PB - Elsevier
SN - 00222860
KW - Density-functional theory
KW - Nuclear magnetic shielding
KW - Conformational analysis
KW - Nucleus-independent chemical shift
KW - Localized molecular orbitals
KW - Berberine
UR - http://dx.doi.org/10.1016/j.molstruc.2012.06.034
L2 - http://dx.doi.org/10.1016/j.molstruc.2012.06.034
N2 - 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).
ER -
KADAM, Shivaji Sambhaji, Jaromír TOUŠEK, Lukáš MAIER, Matej PIPÍŠKA, Vladimír SKLENÁŘ a Radek MAREK. Understanding the NMR properties and conformational behavior of indole vs. azaindole group in protoberberines: NICS and NCS analysis. \textit{Journal of Molecular Structure}. Amsterdam: Elsevier, 2012, roč.~1028, Nov, s.~31-38. ISSN~0022-2860. Dostupné z: https://dx.doi.org/10.1016/j.molstruc.2012.06.034.
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