Synthesis and DFT characterisation of 2-arylamino-1,4-benzoquinone derivatives as potential electron transfer mediators

  • Edita Voitechovič
  • Regina Jančienė
  • Gema Mikulskienė
  • Aušra Vektarienė
  • Gytis Vektaris
  • Julija Razumienė
Keywords: 1,4-benzoquinone, aromatic amine, 2-arylamino-1,4-benzoquinone, NMR spectroscopy, quantum chemical structure–activity relationship (QSAR) descriptors, electron transfer mediator


A series of new potential electron transfer mediators, 2-substituted 1,4-benzoquinone derivatives bearing an arylamino group with various substituents in o-, m- and p-positions of an aromatic ring were synthesised by adding a solution of aniline derivatives in aqueous acetic acid to an aqueous solution of 1,4-benzoquinone. The structure and properties of synthesised compounds were investigated by NMR spectroscopy methods in detail. The redox ability of 2-arylamino-1,4-benzoquinone derivatives has been estimated by calculations of quantum chemical structure– activity relationship (QSAR) descriptors within the framework of density functional theory.
Organic Chemistry