Pyrazinyl and pyridinyl bis-azomethines formation: an experimental and computational study

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F46747885%3A24530%2F23%3A00011371" target="_blank" >RIV/46747885:24530/23:00011371 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/23:10471134

Výsledek na webu

<a href="https://www.nature.com/articles/s41598-023-44585-7" target="_blank" >https://www.nature.com/articles/s41598-023-44585-7</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1038/s41598-023-44585-7" target="_blank" >10.1038/s41598-023-44585-7</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Pyrazinyl and pyridinyl bis-azomethines formation: an experimental and computational study

Popis výsledku v původním jazyce

Formation of bis-azomethines from hydrazine and heterocyclic aromatic carbaldehydes, namely pyridine-2-carbaldehyde and pyrazine-2-carbaldehyde, is studied using density functional theory. The theoretical investigation is correlated with experimental results obtained by means of NMR spectroscopy. The presence of bis-hemiaminal intermediates is evidenced by NMR spectra while surprisingly stable hemiaminal intermediate was isolated experimentally. Water, methanol and acetic acid were outlined to play a crucial role as active catalysts of elementary steps of the reaction mechanisms. The possible reaction sequences, i.e. addition-dehydration-addition-dehydration or addition-addition-dehydration-dehydration are investigated and discussed. Also, alternative mechanistic path via ionic mechanism was proposed for the formation of hemiaminals.

Název v anglickém jazyce

Pyrazinyl and pyridinyl bis-azomethines formation: an experimental and computational study

Popis výsledku anglicky

Formation of bis-azomethines from hydrazine and heterocyclic aromatic carbaldehydes, namely pyridine-2-carbaldehyde and pyrazine-2-carbaldehyde, is studied using density functional theory. The theoretical investigation is correlated with experimental results obtained by means of NMR spectroscopy. The presence of bis-hemiaminal intermediates is evidenced by NMR spectra while surprisingly stable hemiaminal intermediate was isolated experimentally. Water, methanol and acetic acid were outlined to play a crucial role as active catalysts of elementary steps of the reaction mechanisms. The possible reaction sequences, i.e. addition-dehydration-addition-dehydration or addition-addition-dehydration-dehydration are investigated and discussed. Also, alternative mechanistic path via ionic mechanism was proposed for the formation of hemiaminals.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

Scientific Reports

ISSN

2045-2322

e-ISSN

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Svazek periodika

13

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

12

Strana od-do

17383-17394

Kód UT WoS článku

001101655300008

EID výsledku v databázi Scopus

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