
Geography and Environmental Engineering
Johns Hopkins University (Baltimore, MD)
Benzoquinones stable in water such as p-benzoquinone and juglone are sufficiently electrophilic to form Michael-Type adducts with strong, sulfur-donor nucleophiles (e.g. bisulfide ion) but not with environmentally-relevant oxygen- and nitrogen-donor nucleophiles. In our work, dihydroxybenzenes bearing electron-withdrawing acetyl and carboxylic acid groups are oxidized by manganese(III,IV) (hydr)oxides typical of those found at oxic/anoxic interfaces into novel benzoquinones. The novel benzoquinones form adducts with OH-/H2O, anilines, imidazoles, and phenols on timescales of minutes, rather than hours. Mono- and di-adduct products have been confirmed using LC-ESI-MS. Reactions of this kind may contribute to the incorporation of oxygen- and nitrogen-containing chemicals, both natural and synthetic, into natural organic matter

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