Taken together, the trends in spin splitting energies at each intermediate indicate that Ru catalysts could be expected to undergo a spin-forbidden pathway for radical rebound C-H hydroxylation, irrespective of the ligand environment in the catalyst because the ligand field strength plays a limited role in determining the ground state spin for Ru catalysts. Starting from the resting state species in the LS state, the most favorable reaction energetics require that spin crossover occurs to form an IS Ru-oxo species followed by a b-radical transfer during HAT to form a LS Ru-hydroxo species with a ferromagnetically coupled •CH(CH3)2 radical that maintains the overall IS state. Subsequently, another spin crossover event should occur during the rebound of the isopropyl-radical to return to the preferred LS state at the isopropanol-bound intermediate.