Theoretical investigation of the conformational behaviour of the N-phenylbenzohydroxamic acid in solution

Using ab initio theoretical approaches, we investigated the relative stability of two of the possible isomers of N-phenylbenzohydroxamic acid, PhCONOHPh. In particular, within the framework of density functional theory (DFT), we studied the cis and trans conformational isomers of PhCONOHPh, both in the gas phase and in solution. A polarizable continuum model (C-PCM) and a cluster approach were used to simulate the solute-solvent interactions and their effect on the relative stabilities of the isomers. The possible formation of dimers, experimentally postulated, was also taken into account. Finally, C-13 and H-1 NMR spectra were computed and analysed in order to compare them with available experimental data. Copyright (C) 2004 John Wiley Sons, Ltd.