Structure and NMR properties of 6-substituted-5,6-dihydrobenzo[c]phenanthridine alkaloids

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/62157124:16370/13:43871914

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Structure and NMR properties of 6-substituted-5,6-dihydrobenzo[c]phenanthridine alkaloids

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Structure and NMR properties of 6-substituted-5,6-dihydrobenzo[c]phenanthridine alkaloids

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/ED1.1.00%2F02.0068" target="_blank" >ED1.1.00/02.0068: CEITEC - central european institute of technology</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Physical Organic Chemistry

ISSN

0894-3230

e-ISSN

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Svazek periodika

26

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

8

Strana od-do

814-821

Kód UT WoS článku

000325936700009

EID výsledku v databázi Scopus

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