One-Electron Reduction Potential and Ring Opening of the Succinimidyl Radical in Water

Article abstract of DOI:10.1021/j100110a023

By means of pulse radiolysis in water, N-chlorosuccinimide (SCl) was reduced in a one-electron step to yield the succinimidyl radicals, S^*, via the intermediacy of the radical anion, SCl^*-.The rate of ring opening of S^* was measured to be 8 x 10⁴ s^-1.By equilibrium with Cl2^*-/2Cl^-, the one-electron reduction potential of S^* was determined to be 2.22 +/- 0.02 V vs NHE.From this value and other data, the N-H bond strength in succinimide was calculated to be 118 +/- 3 kcal/mol.