Publication details

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

Authors

KONHEFR Martin LACINA Karel SKRUTKOVÁ LANGMAJEROVÁ Monika GLATZ Zdeněk SKLÁDAL Petr MAZAL Ctibor

Year of publication 2018
Type Article in Periodical
Magazine / Source ChemistrySelect
MU Faculty or unit

Faculty of Science

Citation
Web http://onlinelibrary.wiley.com/doi/10.1002/slct.201802030
Doi http://dx.doi.org/10.1002/slct.201802030
Keywords B–N Interaction; Boronic Acid; Ferrocene; Hemiaminal; Imine
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.
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