Reductive dechlorination pathways for substituted benzenes: a correlation with electronic properties |
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Authors: | Cynthia L Cozza Sandra L Woods |
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Institution: | (1) Landau Associates, 23107 100th Ave. W., 98020 Edmonds, Washington;(2) Environmental and Water Resources Engineering Program, Department of Civil Engineering, Oregon State University, Apperson 202, 97331-2302 Corvallis, Oregon, USA |
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Abstract: | Electronic properties were correlated with observed reductive dechlorination pathways by unacclimated consortia for chlorinated phenols, dihydroxybenzenes, benzoic acids, and anilines. Molecular structures and properties were calculated using the semi-empirical Modified Neglect of Differential Overlap method at the Cornell Supercomputing Facility. Observed preferential positions for reductive dechlorination by unacclimated consortia correlate well with the largest negative value for the carbon-chlorine bond charge. Of 16 dechlorination pathways observed for unacclimated bacteria, the most negative carbon-chlorine bond charge correlated with 15 pathways.This correlation between the observed dechlorination position and the parent compound's electronic properties is consistent with the observed reductive dechlorination of chlorophenols and chlorinated dihydroxybenzenes at the ortho position, and the meta dechlorination of chlorobenzoic acids. Net carbonchlorine bond charges also correlate with the preferred dechlorination position for two of three known chloroaniline pathways, suggesting preferential removal of chlorines from the ortho position of chloroanilines.Abbreviations CA
chloroaniline
- CBz
chlorobenzoic acid
- CC
chlorocatechol
- CP
chlorophenol
- DCA
dichloroaniline
- DCBz
dichlorobenzoic acid
- DCC
dichlorocatechol
- DCH
dichlorohydroquinone
- DCP
dichlorophenol
- DCR
dichlororesorcinol
- PCP
pentachlorophenol
- TCA
trichloroaniline
- TCBz
trichlorobenzoic acid
- TCC
trichlorocatechol
- TCH
trichlorohydroquinone
- TCP
trichlorophenol
- TCR
trichlororesorcinol
- TeCA
tetrachloroaniline
- TeCBz
tetrachlorobenzoic acid
- TeCC
tetrachlorocatechol
- TeCH
tetrachlorohydroquinone
- TeCP
tetrachlorophenol
- TeCR
tetrachlororesorcinol |
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Keywords: | anaerobic biodegradation chlorinated dihydroxybenzenes chloroanilines chlorobenzoates chlorophenols reductive dechlorination |
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