Effect of adjacent electron pair on the thermodynamic stabilities of some nitrogen-centered radicals and anions

DURING the past two decades Bordwell and co-workers have built up an extensive collection of the equilibrium acidity constants (pK) in DMSO solution which now includes over a thousand of organic compounds of a wide range of structures. Later, Bordwell and Parker, as well as our group have developed the methods for estimating homolytic cleavage energies (BDE) of the acidic R-H bonds in DMSO, water, and in the gas phase, respectively, from properly designed thermodynamic cycles utilizing the pKand redox data which can be