Accurate O-H...O hydrogen-bond dissociation energies were measured for the supersonic-jet-cooled complexes 1-naphthol.S with S=D2O, ethanol, oxirane, and oxetane. A mass-selective pump-dump-probe method was used, combining stimulated emission pumping with resonant two-photon ionization and ion-dip techniques. The ground-state dissociation energies D-0(S-0) are 5.83+/-0.13 kcal/mol for d(1)-1-naphthol.D2O, 7.94+/-0.02 kcal/mol for 1-naphthol.ethanol, 7.71+/-0.14 kcal/mol for 1-naphthol.oxirane and >8.17 kcal/mol for 1-naphthol.oxetane. The D-0's increase by 5%-7% upon excitation of 1-naphthol to the S-1 state. These dissociation energies are compared to those of the analogous complexes with S=H2O, methanol, NH3, and ND3 [Chem. Phys. Lett. 246, 291 (1996)]. The trends in D-0 are compared to the electric dipole moments mu, molecular polarizabilities (α) over bar, and gas-phase proton affinities of the H bond acceptor molecules. For the O-containing acceptors, the D-0's correlate well with (α) over bar, but the only good overall correlation for both O- and N-containing acceptors was found between the dissociation energies and proton affinities.