Proton affinity and gas-phase basicity of pyrogallol and phloroglucinol: a computational study

We report the proton affinities (PAs) and gas-phase basicities (GBs) of pyrogallol (1,2,3-trihydroxybenzene) phloroglucinol (1,3,5-trihydroxybenzene), as determined by high level quantum chemical calculations a series isodesmic transfer reactions. These yet unmeasured values have relevance to release active species from nanocarriers derived calixarene family macrocycles. The PAs GBs obtained for these two trihydroxybenzene isomers are compared contrasted with those previously third isomer, hydroxyquinol (1,2,4-trihydroxybenzene). Preferred protonation sites relative thermochemical analyzed in terms electron delocalization effects consequent disruption intramolecular hydrogen bonding.