Here, we report on a novel and facile way to form [1 •-]([X + ]) (X=Li, Na, K), by employing a wide variety of simple anionic organic bases in different solvents at room temperature (Scheme 1). Exhaustive EPR characterization coupled to detailed density functional theory calculations support the reduction of [1] via single electron transfer (SET) from the anionic organic base -while SET is calculated to be slightly endothermic for most cases, further transformations of the resulting oxidised bases render the overall process thermodynamically favourable. To the best of our knowledge, this is the first time that nitrobenzenide [1 •-]([X + ]) is shown to occur thermally via direct SET from anionic organic bases, echoing frustrated radical pairs. Our results present the added value of unlocking the extensive family of nitroarenes as platforms to implement radical-based chemistry, conveniently and directly from commercially available reagents, showing that these commonplace molecules still have lot to offer. 45