Chemical structure and biodegradability of halogenated aromatic compounds substituent effects on 1,2-dioxygenation of benzoic acid

摘要: Abstract Dioxygenation of substituted benzoic acid by whole cells 3-chlorobenzoate-utilizing Pseudomonas sp. B13, benzoate-induced Alcaligenes eutrophus B 9 and toluate-grown putida mt-2 was examined. Electron-attracting substituents like halogen decreased the reaction rates benzoate 1,2-dioxygenation. acids P. mostly undisturbed steric effects substituents. Good correlation resulted between log V rel values Hammett substituent constant σ. In contrast dioxygenation 13 A. were predominantly A non-polar mechanism 1,2-dioxygenation is discussed. Results from inhibition studies demonstrate high stereospecificities for with in ortho- or para-position. case handrance observed only ortho-substituted acids. Stereospecificities are illustrated schematically.