General methods and instrumentation. All reactions were performed at room temperature in an N2-filled glovebox or by using standard Schlenk techniques unless otherwise specified. Glassware was oven dried at 150 o C for at least 2h prior to use, and allowed to cool under vacuum. All reagents were used as received unless otherwise stated. Anhydrous pentane, CH3CN, diethyl ether, benzene, toluene and THF were purified by sparging with nitrogen for 30 minutes and then passing under nitrogen pressure through a column of activated A2 alumina. NMR solvents were purchased from Cambridge Isotope Laboratories. C6D6 was degassed by three freeze-pump-thaw cycles and dried over freshly activated 3 Å molecular sieves for 24 hours prior to use. Paramagnetic 1 H NMR spectra were recorded on Bruker 400 MHz or 600 MHz instruments, with shifts reported relative to the residual solvent peak. Elemental analyses were performed at the University of California Berkeley. FTIR measurements were carried out on a Thermo Scientific Nicolet iS20 spectrometer. UV-vis measurements were carried out on a Hewlett Packard 8453 UV-Visible spectrophotometer. Electrochemical measurements were carried out using a BioLogic SP50 potentiostat. Magnetic susceptibility measurements were carried on a Quantum Design MPMS XL instrument running MPMS Multivu software. Powdered, crystalline samples were placed inside a custommade quartz tube, vacuum sealed, and suspended in a plastic straw. Fitting simulations were performed using PHI. The following compounds were synthesized according to published procedure: Co[N(SiMe3)2]2(THF), 1,3,5-tris(2-bromophenyl)-benzene, O-(2,4-dinitrophenyl)-hydroxylamine, di(1-adamantyl)phosphine. Detailed information on the synthesis of Int1, NMR spectra, X-ray diffraction, and DFT calculations are provided in the Supporting Information. Caution! The electrophilic aminating agent O-(2,4-dinitrophenyl)-hydroxylamine and its derivatives are potentially energetic compounds in pure form. Preparations of this reagent as described typically afford material that is ~95% pure, can be handled in air, and stored at -35 o C for months without noticeable decomposition. Representative samples do not exhibit characteristics of a thermallyinduced explosive (Fig S1) and are resistant to compression shock and sparks. Owing to the explosive nature of pure 2,4-dinitrophenol in air, all necessary safety precautions should be undertaken when handling the 2,4-dinitrophenolate intermediates derived from the amination procedures. Specifically, heating of reaction mixtures should be avoided, all manipulations should be performed under an inert atmosphere, and reaction byproducts should be diluted with water prior to disposal.