6533b822fe1ef96bd127cae1

RESEARCH PRODUCT

(o-Hydroxyphenyl)methylphosphonic acids: Synthesis and potentiometric determinations of their pKaValues

Salah ChafaaJean MeullemeestreVolker BöhmerMarie-josé SchwingF. VierlingWalter Vogt

subject

Steric effectsChemistryOrganic ChemistryPotentiometric titrationRing (chemistry)BiochemistryMedicinal chemistryCatalysisInorganic Chemistrychemistry.chemical_compoundHydrolysisDrug Discoveryheterocyclic compoundsHydroxymethylPhenolsPhysical and Theoretical Chemistry

description

(o-Hydroxyphenyl)methylphosphonic acids are readily obtained from o-(bromomethyl)- or o-(hydroxymethyl)phenols and trialkyl phosphites. Subsequent hydrolysis leads to the corresponding phosphonic acids. For a series of such compounds, the pKa values have been determined by potentiometry. Their dependence on additional substituents in the aromatic ring is discussed in terms of electronic and steric effects.

https://doi.org/10.1002/hlca.19930760108