Toggle Main Menu Toggle Search

Open Access padlockePrints

Influence of substituents on reductive dehalogenation of 3-chlorobenzoate analogs

Lookup NU author(s): Dr Jan DolfingORCiD


Full text for this publication is not currently held within this repository. Alternative links are provided below where available.


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.

Publication metadata

Author(s): Dolfing J, Tiedje JM

Publication type: Article

Publication status: Published

Journal: Applied and Environmental Microbiology

Year: 1991

Volume: 57

Issue: 3

Pages: 820-824

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 English Article APPL ENVIRON MICROBIOL FA764