Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Electrochemically Facilitated Interaction of O-Nucleophiles with Imine Group in Electroactive ortho-((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ChemistrySelect
ISSN
2365-6549
e-ISSN
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Volume of the periodical
3
Issue of the periodical within the volume
33
Country of publishing house
DE - GERMANY
Number of pages
7
Pages from-to
9641-9647
UT code for WoS article
000443936200020
EID of the result in the Scopus database
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