Structural characterization and electrochemical properties of the 3,3'-5,5'-tetra-tert-butyl-4,4'-diphenoquinone

Crystals of the 3,3'-5,5'-tetra-tert-butyl-4,4'-diphenoquinone (TTBDQ) in the reaction mixture DCM/MeOH (1:1, v/v) were obtained as a result of CC coupling reaction of the sterically hindered phenol (2,6-di-tert-butylphenol, DTBP) using the binuclear Co(II) complexes. The oxidation product (TTBDQ), C(28)H(40)O(2), crystallizes in the space group P1 with one-half molecule in the asymmetric unit and the other half generated by an inversion centre. The diphenoquinone moiety is planar within +/-0.016(3)A. The crystal structure is stabilized by intramolecular C-H...O hydrogen bonds. The spectroscopic and electrochemical properties of the TTBDQ also have been studied.