On the Mechanism of the Reaction of o‐Benzenesulfonamido‐p‐benzoquinone with Ammonia and Amines

Abstract

In the determination of ammonia in sera using o-benzenesulfonamido-pbenzoquinone proteins cause false positive results. These findings contradict the reaction mechanism postulated in lit., according to which a dimer is formed through an NH-bridge. As deduced by 'H-NMR-, IR-, UV-, and mass spectroscopic investigations of the reaction product and by semiempirical MO-calculations, charge transfer (CT')-complexes 3a are formed with ammonia as well as with proteins, amino acids, and amines. These CT-complexes are in a solvent dependent equilibrium with their salts 3b. Depending on the electron density of the m i n e compound, different subsequent products may be formed.