Radical cations of 1,2-bis(dialkylamino)benzenes: Restricted rotation about the C-NMe2 bond

Article abstract of DOI:10.1016/S0040-4039(00)76959-0

The 1,2-bis(dialkylamino)benzene radical cations 2a-c^.+ were generated by oxidation of the parent compounds with iodine or lead tetraacetate. ESR and ENDOR studies of 2a^.+ and 2b^.+ gave evidence of a restricted rotation about the C-NMe₂ bond; based on the results of 2c^.+ the different N-methyl proton splittings in 2a⁺⁺ and 2b^.+ were assigned to the exo and endo N-methyl groups.