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PHOTOCHEMICAL TRANSFORMATIONS IN SALICYLANILIDE PHOTOALLERGY
Author(s) -
EPLING GARY A.,
WELLS JENNIE L.,
YOON UNG CHAN
Publication year - 1988
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1988.tb02709.x
Subject(s) - chemistry , dimer , halogenation , photochemistry , photodissociation , primary (astronomy) , hydrogen atom abstraction , radical , organic chemistry , physics , astronomy
— The photochemical transformations of 3,3′,4′,5‐tetrachlorosalicylanilide, have been characterized by isolation and spectroscopic determination of the primary and secondary photoproducts. The photoreactivity cleanly involves photochemical dechlorination; three chlorines are ultimately lost in an efficient stepwise fashion. A radical mechanism was implicated by formation of a dimer and hydrogen atom abstraction from cysteine when present during photolysis. In the presence of HSA or BSA, the initial dehalogenation leads to a photoadduct with the protein, but dehalogenation of the primary photoproduct, a trichloro compound, does not lead to an efficient photobinding to protein.