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Reductive bond cleavage of chloro-substituted 10-methyl- tribenzotriquinacenes: Transition between concerted and stepwise mechanisms

Authors
Journal
Electrochimica Acta
0013-4686
Publisher
Elsevier
Publication Date
Volume
51
Issue
27
Identifiers
DOI: 10.1016/j.electacta.2005.11.050
Keywords
  • Centropolyindanes
  • Cyclic Voltammetry
  • Radical Anions
  • Bond Cleavage
  • Concerted Mechanism
Disciplines
  • Chemistry

Abstract

Abstract The electrochemical reduction of 1-chloro-, 1,4-dichloro- and 1,4,7-trichloro-10-methyl-tribenzotriquinacenes in ACN and DMF was found to occur by concerted electron transfer and bond breaking process, showing irreversible cyclic voltammetric peaks. However, the transition of the process to the stepwise mechanism upon increasing the driving force by raising the scan rate was established. Both C Cl bonds are reduced successively in the dichloro compound, but only two bonds overall were reduced in the trichloro compound. The reduction mechanism is discussed. The homolytic dissociation energy of C Cl bond in monochloro compound was estimated to be equal to 2.9 eV.

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