The role of hydrogen bonding on the H-atom-donating abilities of catechols and naphthalene diols and on a previously overlooked aspect of their infrared spectra

Kinetic effects on H-atom abstractions from the diols in HB acceptor (HBA) solvents can be quantitatively accounted for over at least 50% of the available range of solvent HBA activities on a basis of a single reactive OH group, the 'free' OH. The shift in frequency of the intramolecularly H-bonded OH group of suitable diols in CCl4 induced by low concentrations of additives might be a quick and simple method for estimating beta2H values.