Acidities and homolytic bond dissociation enthalpies (BDEs) of the acidic H-A bonds in acyclic and cyclic alkoxycarbonyl compounds (esters and carbamates)

A comparative study reveals the higher equilibrium of C-H bond acidities of three cyclic carboxylic esters having alkoxycarbonyl group locked in an E conformation than those of their acyclic analogues. N-H acidity of acyclic carbamates having alkoxycarbonyl group locked in an E conformation is higher than that of acyclic analogous. However, the structural changes exhibit no influence on the bond dissociation energies of the acidic C-H or N-H bonds in the esters or carbamates.