Monatshefte für Chemie - Chemical Monthly

, Volume 146, Issue 5, pp 857–862 | Cite as

Influence of structure on electrochemical reduction of isomeric mono- and di-, nitro- or nitrosocalix[4]arenes

  • Alan Liška
  • Karolína Flídrová
  • Pavel Lhoták
  • Jiří Ludvík
Original Paper

Abstract

A newly synthesized series of mono- and di-, nitro- or nitrosocalix[4]arenes has been investigated electrochemically. It was shown that besides the fundamental redox characterization, the electrochemical data contain also information about the space arrangement of the molecule as well as about dynamic 3D changes. The interpretation is based on the comparison of observed electrochemical behavior of homologous couples or triads taken from the studied series of compounds. Using the nitro and nitroso group as a redox probe, it was found that unsubstituted or para-nitro-substituted cone-calixarenes are flexible, exhibiting in solution a periodic pinched cone–pinched cone interconversion, whereas the 1,3-alt conformation or any meta-substitution causes rigidity of the whole skeleton. All aromatic nitro and nitroso groups in calixarenes appeared to be reducible at the same potential showing their electronic independency on the rest of the molecule.

Graphical abstract

Keywords

Nitrocalix[4]arenes Nitrosocalix[4]arenes Electrochemical reduction Redox probe 

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Copyright information

© Springer-Verlag Wien 2015

Authors and Affiliations

  • Alan Liška
    • 1
    • 2
  • Karolína Flídrová
    • 3
  • Pavel Lhoták
    • 3
  • Jiří Ludvík
    • 1
  1. 1.Department of Molecular ElectrochemistryJ. Heyrovský Institute of Physical Chemistry AS CRPrague 8Czech Republic
  2. 2.Department of Inorganic Chemistry, Faculty of ScienceCharles University in PraguePrague 2Czech Republic
  3. 3.Department of Organic ChemistryInstitute of Chemical Technology, PraguePrague 6Czech Republic

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