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Lookup NU author(s): Dr Jan DolfingORCiD
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The biochemical effects of aryl substituents on the reductive dechlorination of 3-chlorobenzoate analogs were quantified with (i) a stable 3-chlorobenzoate-grown methanogenic sludge enrichment, (ii) Desulfomonile tiedjei DCB-1, isolated from this enrichment and able to catalyze the reductive dechlorination of 3-chlorobenzoate, and (iii) a defined 3-chlorobenzoate-degrading methanogenic consortium with D. tiedjei as the key dechlorinating organism. The addition of hydrogen stimulated the dechlorination rate in the consortium. The extent of this stimulation depended on the substituent. The data were evaluated with various sets of substituent constants compiled for the Hammett equation. None of the sets yielded a satisfactory correlation between experimental values and theoretical constants. This suggests that the microbially catalyzed reductive dechlorination of 3-chlorobenzoate cannot be described simply as either a nucleophilic or an electrophilic substitution reaction. Nevertheless, observations that the presence of a para-amino or -hydroxy group inhibited the rate of dechlorination suggest that the rate-limiting step in the reductive dechlorination of 3-chlorobenzoate is a nucleophilic attack on the negatively charged pi-electron cloud around the benzene nucleus.
Author(s): Dolfing J, Tiedje JM
Publication type: Article
Publication status: Published
Journal: Applied and Environmental Microbiology
Print publication date: 01/03/1991
ISSN (print): 0099-2240
ISSN (electronic): 1098-5336
Publisher: American Society for Microbiology
Notes: Times Cited: 23
Cited Reference Count: 36
APPL ENVIRON MICROBIOL