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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

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • 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

  • 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