| KONHEFR, Martin, Karel LACINA, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL a Ctibor MAZAL. Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers. ChemistrySelect. Weinheim: WILEY-VCH Verlag GmbH & Co. KGaA, 2018, roč. 3, č. 33, s. 9641-9647. ISSN 2365-6549. Dostupné z: https://dx.doi.org/10.1002/slct.201802030. |
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@article{1432817,
author = {Konhefr, Martin and Lacina, Karel and Skrutková Langmajerová, Monika and Glatz, Zdeněk and Skládal, Petr and Mazal, Ctibor},
article_location = {Weinheim},
article_number = {33},
doi = {http://dx.doi.org/10.1002/slct.201802030},
keywords = {B–N Interaction; Boronic Acid; Ferrocene; Hemiaminal; Imine},
language = {eng},
issn = {2365-6549},
journal = {ChemistrySelect},
title = {Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers},
url = {http://onlinelibrary.wiley.com/doi/10.1002/slct.201802030},
volume = {3},
year = {2018}
}
TY - JOUR
ID - 1432817
AU - Konhefr, Martin - Lacina, Karel - Skrutková Langmajerová, Monika - Glatz, Zdeněk - Skládal, Petr - Mazal, Ctibor
PY - 2018
TI - Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers
JF - ChemistrySelect
VL - 3
IS - 33
SP - 9641-9647
EP - 9641-9647
PB - WILEY-VCH Verlag GmbH & Co. KGaA
SN - 23656549
KW - B–N Interaction
KW - Boronic Acid
KW - Ferrocene
KW - Hemiaminal
KW - Imine
UR - http://onlinelibrary.wiley.com/doi/10.1002/slct.201802030
L2 - http://onlinelibrary.wiley.com/doi/10.1002/slct.201802030
N2 - 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.
ER -
KONHEFR, Martin, Karel LACINA, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL a Ctibor MAZAL. Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers. \textit{ChemistrySelect}. Weinheim: WILEY-VCH Verlag GmbH \&{} Co. KGaA, 2018, roč.~3, č.~33, s.~9641-9647. ISSN~2365-6549. Dostupné z: https://dx.doi.org/10.1002/slct.201802030.
|
