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

Abstract

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 (kb) 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 van der Waals radius of the substituent group with log kb gave correlation coefficients (r2) 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 tra,nsformation pathway involves oxidative deamination of the anilines.

A new biodegradation prediction model specific to petroleum hydrocarbons

“…Other biodegradation models have been developed for select groups of structurally similar compounds [7]. For example, models have been developed to predict the biodegradation of a limited number of alcohols [8], n-alkyl phthalates [9], chlorophenols and chloroanisoles [10], para-substituted phenols [11], and meta-substituted anilines [12]. However, these models were developed using a single group of structurally similar compounds, and they are based on a single degradation mechanism.…”

Infrared Spectroscopy-Based Property-Reactivity Correlations for Predicting Environmental Fate of Organic Chemicals

“…The kBo values of aniline and six m-substituted (bromo, chloro, methyl, methoxy, nitro, and cyano) anilines were taken from the literature [4]. These compounds were oxidatively deaminated to the corresponding catechols by an aniline-grown pure culture isolated from the Oconee River in northern Georgia.…”

“…These compounds were oxidatively deaminated to the corresponding catechols by an aniline-grown pure culture isolated from the Oconee River in northern Georgia. This transformation involved dioxygenases incorporating two atoms of molecular oxygen [4]. The IR spectra of all of these anilines, except p-cyano-and p-nitroaniline, were recorded as thin films between KBr disks.…”

“…Unfortunately, we know of no sets of data for which reliable rates of microbial transformations have been determined by using a consistent method for 30 or more well-chosen compounds in a single structural class. There are, however, a number of published reports of rate constants for sets of 6 to 10 members of selected classes for which constants have all been measured in the same laboratory, using a single, reproducible protocol [3,4,9,11]. Therefore, we have investigated the correlations of discrete peak parameters with rate constants for these selected classes, with the assumption that if correlations similar to those in Figures 1 and 2 existed, then the superior FT-based prediction system could be extended to microbial degradation when more data were available.…”

“…Microbially mediated oxidation of anilines. As a result of their observations with the microbial oxidation of phenols [3], Paris and Wolfe [4] investigated the microbial oxidation of aniline and seven m-substituted anilines. Again, they found a good correlation of log kBO and the van der Waal's radius of the substituent ( r 2 = 0.924).…”