Structure and NMR properties of 6-substituted-5,6-dihydrobenzo[c]phenanthridine alkaloids
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F13%3A00068644" target="_blank" >RIV/00216224:14310/13:00068644 - isvavai.cz</a>
Alternative codes found
RIV/62157124:16370/13:43871914
Result on the web
<a href="http://dx.doi.org/10.1002/poc.3175" target="_blank" >http://dx.doi.org/10.1002/poc.3175</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/poc.3175" target="_blank" >10.1002/poc.3175</a>
Alternative languages
Result language
angličtina
Original language name
Structure and NMR properties of 6-substituted-5,6-dihydrobenzo[c]phenanthridine alkaloids
Original language description
We report a preparation of new 6-substituted-5,6-dihydrobenzo[c]phenanthridines by the reaction of azoles with quaternary benzo[c]phenanthridine alkaloids sanguinarine and chelerythrine. The prepared compounds have been characterized by NMR spectroscopy,mass spectrometry, and single-crystal X-ray diffraction. Conformational behaviors of carbazole derivatives in solution have been investigated by low-temperature NMR experiments. Barriers to rotation around newly formed C6?N bonds were determined to be 12?13 kcal/mol. Quantum chemical calculations have been used to reproduce the experimental observations. Large structural effects on several 1H NMR resonances were observed experimentally, analyzed by DFT calculations at B3LYP/6-311+G(d,p)/PCM level, andinterpreted by ring-current effects of the benzo[c]phenanthridine and carbazole units.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/ED1.1.00%2F02.0068" target="_blank" >ED1.1.00/02.0068: Central european institute of technology</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Physical Organic Chemistry
ISSN
0894-3230
e-ISSN
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Volume of the periodical
26
Issue of the periodical within the volume
10
Country of publishing house
US - UNITED STATES
Number of pages
8
Pages from-to
814-821
UT code for WoS article
000325936700009
EID of the result in the Scopus database
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