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Two‐dimensional NMR studies of arsenical‐sulfhydryl adducts
Author(s) -
O'Connor Richard J.,
McGown Evelyn L.,
Dill Kilian,
Hallowell Susan F.
Publication year - 1989
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260270713
Subject(s) - chemistry , adduct , antidote , nuclear magnetic resonance spectroscopy , arsenic , stereochemistry , carbon 13 nmr , medicinal chemistry , organic chemistry , toxicity
British anti‐lewisite (2,3‐dimercaptopropanol) (BAL) has long been used as an arsenic antidote, but its therapeutic efficacy is limited by its inherent toxicity. Two less toxic potential replacements for BAL are dimercaptosuccinic acid and dimercaptopropanesulfonic acid. These two disulfhydryl compounds were compared with BAL by studying the structures of their adducts with two organic arsenicals, phenyldichloroarsine and trans ‐2‐chlorovinylarsine oxide. The 1:1 adducts were synthesized and characterized by one‐ and two‐dimensional NMR spectroscopy. 1 H and 13 C spectral data and resonance assignments, verified by spin simulation, are presented for the adducts. All were five‐membered heteroatomic ring systems, with different solubility properties. When stereoisomers were detectable, the ratio of anti to syn isomers varied, indicating that the functional group of the antidote influenced stereochemical aspects of adduct formation.