Ab initio study of solvent effects on the acetohydroxamic acid deprotonation processes

The aim of this paper is to compare ab initio calculations performed in solution using two different approaches where the solvent is treated as a continuum of constant permittivity. Two different solvents are studied: acetone and water. The calculated solvation energies in water with the PCM model directly applied on the isolated species are compared to those determined building the molecular aggregates with one water molecule. In all cases studied, the N-deprotonation of the Z-amide is the most probable process. Since more than one deprotonation process has been experimentally observed, the relative probabilities of the O-deprotonation of the Z-amide, and the N- and O-deprotonation of the E-amide forms are discussed. The probability of N-deprotonation from the Z-amide form increases in acetone.