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On the Mechanism of the Reaction of o ‐Benzenesulfonamido‐ p ‐benzoquinone with Ammonia and Amines
Author(s) -
Gündisch Daniela,
Kovar KarlArtur
Publication year - 1994
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19943270110
Subject(s) - chemistry , dimer , ammonia , benzoquinone , amine gas treating , reaction mechanism , solvent , reaction intermediate , medicinal chemistry , electron transfer , photochemistry , stereochemistry , organic chemistry , catalysis
In the determination of ammonia in sera using o ‐benzenesulfonamido‐ p ‐benzoquinone 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 1 H‐NMR‐, IR‐, UV‐, and mass spectroscopic investigations of the reaction product and by semi‐empirical 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 amine compound, different subsequent products may be formed.