Relationship between properties of a series of anilines and their transformation by bacteria

Journal Article · Fri May 01 04:00:00 UTC 1987 · Appl. Environ. Microbiol.; (United States)

OSTI ID:6351124

Paris, D F; Wolfe, N L

The effect of compound structure on the microbial transformation of a series of substituted anilines was investigated. For the pure-culture and environmental water samples studied, the rate of transformation of the compounds decreased in the following order: aniline > 3-bromoaniline > 3-chloroaniline > 3-methylaniline > 3-methoxyaniline > 3-nitroaniline > 3-cyanoaniline. Second-order rate constants (k/sub b/) for each compound was calculated by using bacterial and compound concentrations measured as a function of time. The rate constants correlated with steric parameters. Water samples also were used in kinetic studies with three of the compounds (aniline, 3-chloroaniline, and 3-nitroaniline) to test the relationships with mixed bacterial populations. A simple linear regression of the van der Walls radius of the substituent group with log k/sub b/ gave correlation coefficients (r/sup 2/) of 0.924 for the river isolate and 0.99 for the mixed populations. Analyses of pure-culture and mixed-population samples by thin-layer chromatography indicate that the primary products are catechols. This finding suggests that the transformation pathway involves oxidative deamination of the anilines.

• Research Organization: Environmental Protection Agency, Athens, GA
• OSTI ID: 6351124
• Journal Information: Appl. Environ. Microbiol.; (United States), Journal Name: Appl. Environ. Microbiol.; (United States) Vol. 53:5; ISSN AEMID
• Country of Publication: United States
• Language: English

Related Subjects

560300* -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AMINES
ANILINE
AROMATICS
BACTERIA
BIOLOGICAL PATHWAYS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DEAMINATION
METABOLISM
MICROORGANISMS
ORGANIC COMPOUNDS
SEPARATION PROCESSES
THIN-LAYER CHROMATOGRAPHY