Anodic Oxidation of 18 Halogenated and/or Methylated Derivatives of CB11H12

Abdul Wahab; Christos Douvris; Jiří Klíma; Filip Šembera; Juri Ugolotti; Jiří Kaleta; Jiří Ludvík; Josef Michl

doi:10.1021/acs.inorgchem.6b02126

Anodic Oxidation of 18 Halogenated and/or Methylated Derivatives of CB₁₁H₁₂

Inorg Chem. 2017 Jan 3;56(1):269-276. doi: 10.1021/acs.inorgchem.6b02126. Epub 2016 Dec 12.

Authors

Abdul Wahab^{1

2}, Christos Douvris³, Jiří Klíma², Filip Šembera¹, Juri Ugolotti¹, Jiří Kaleta¹, Jiří Ludvík², Josef Michl^{1

3}

Affiliations

¹ Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Flemingovo nám. 2, 16610 Prague 6, Czech Republic.
² J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic , Dolejškova 3, 18223 Prague 8, Czech Republic.
³ Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80309-0215, United States.

PMID: 27936641
DOI: 10.1021/acs.inorgchem.6b02126

Abstract

Anodic oxidation of [CB₁₁H₁₂]^- and 18 of its halogenated and/or methylated derivatives was examined. Reversible oxidation was found for four of the anions in liquid SO₂ and for four more in 1,1,1,3,3,3-hexafluoroisopropyl alcohol. The oxidation occurred at ∼1 V (for [CB₁₁Me₁₂]^-) up to more than 4 V (for [1-H-(2-6)-F₅-(7-12)-(CF₃)₆-CB₁₁]^-) relative to ferrocene/ferricinium. The anodic peak potentials are reproduced by a set of additive position-sensitive substituent increments.