Open AccessThe mechanism of the iodination of aminochromes
Author(s) -
G. L. Mattok,
D. L. Wilson
Publication year - 1967
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v67-280
Subject(s) - chemistry , halogenation , iodine , iodide , aqueous solution , catalysis , reaction rate , base (topology) , inorganic chemistry , reaction mechanism , medicinal chemistry , photochemistry , organic chemistry , mathematical analysis , mathematics
The kinetics of the iodination of several aminochromes by iodine in aqueous potassium iodide, to form the 7-iodo derivatives, have been studied. The rate of iodination is directly dependent on the concentrations of the aminochrome and iodine and varies inversely with the first power of the iodide ion concentration. The rate of reaction is independent of pH, but the reaction is subject to general base catalysis. A mechanism for the iodination of aminochromes is proposed. The reactive species are molecular iodine and the zwitterionic form of adrenochrome, and the reaction proceeds via a quinonoid intermediate. The rate-controlling process is the removal of the C-7 proton.
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