Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F18%3A00101138" target="_blank" >RIV/00216224:14310/18:00101138 - isvavai.cz</a>

Výsledek na webu

<a href="http://onlinelibrary.wiley.com/doi/10.1002/slct.201802030" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/slct.201802030</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/slct.201802030" target="_blank" >10.1002/slct.201802030</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers

Popis výsledku v původním jazyce

Mutual position of imine and boronic acid moieties in ortho regioisomer of ((ferrocenylimino)methyl)phenylboronic acid (1a) facilitates and highly favours reversible molecular switching between C=N imine and COR-NH hemiaminal group. These two states are controllable electrochemically by oxidation/reduction of ferrocenyl moiety and thus a simple dynamic molecular switch for addition/elimination of nucleophile to/from the imine is formed. The exceptional redox behaviour of 1a in protic primary alcohols is caused by the interaction of both the motif of the boronic acid moiety and imine carbon atom with the alcohol molecule. Thus, the behaviour of acids 1 is influenced by the type of solvent, oxidation state of the ferrocenyl residue and proximity of the boronic acid moiety. Moreover, other multiple equilibria covering majority of possible interactions of imine group and boronic acid moiety with surroundings including influence of various O-nucleophiles have been addressed and described in detail within the interest in understanding the fundamental factors governing the B–N interaction.

Název v anglickém jazyce

Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers

Popis výsledku anglicky

Mutual position of imine and boronic acid moieties in ortho regioisomer of ((ferrocenylimino)methyl)phenylboronic acid (1a) facilitates and highly favours reversible molecular switching between C=N imine and COR-NH hemiaminal group. These two states are controllable electrochemically by oxidation/reduction of ferrocenyl moiety and thus a simple dynamic molecular switch for addition/elimination of nucleophile to/from the imine is formed. The exceptional redox behaviour of 1a in protic primary alcohols is caused by the interaction of both the motif of the boronic acid moiety and imine carbon atom with the alcohol molecule. Thus, the behaviour of acids 1 is influenced by the type of solvent, oxidation state of the ferrocenyl residue and proximity of the boronic acid moiety. Moreover, other multiple equilibria covering majority of possible interactions of imine group and boronic acid moiety with surroundings including influence of various O-nucleophiles have been addressed and described in detail within the interest in understanding the fundamental factors governing the B–N interaction.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

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

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

ChemistrySelect

ISSN

2365-6549

e-ISSN

—

Svazek periodika

3

Číslo periodika v rámci svazku

33

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

7

Strana od-do

9641-9647

Kód UT WoS článku

000443936200020

EID výsledku v databázi Scopus

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