Phenol O-H bond dissociation energy in water clusters

We are reporting ab initio and density functional theory (DFT) calculations for the phenol O-H bond dissociation energy in the gas phase and in phenol-water clusters. We have tested a series of recently proposed functionals and verified that DFT systematically underestimates the O-H bond dissociation energy of phenol. However, O-H bond dissociation energies in water clusters are in reasonable agreement with experimental data for phenol in solution. We. have evaluated electronic difference densities in phenol-water, phenoxy-water, and water, and we are suggesting that the representation of this quantity gives an interesting picture of the electronic density rearrangement induced by hydrogen bond interactions in phenol-water clusters. (C) 2002 John Wiley & Sons, Inc.