Covalent binding of aniline to humic substances and whole soil organic matter

Conference · Sun Dec 31 04:00:00 EST 1995

OSTI ID:214886

Thorn, K A; Goldenberg, W S; Younger, S J ^[1]

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1. Geological Survey, Arvada, CO (United States)

Aromatic amines enter the environment from the chemical or microbial degradation of dyes, explosives, and the acylanilide, phenylcarbamate, and phenylurea classes of herbicides. One possible fate of aromatic amines in soils is covalent binding to naturally occurring organic matter. The binding of {sup 15}N-labelled aniline to the fulvic and humic acids extracted from an Elliot silt loam soil with and without catalysis by peroxidase or birnessite has been examined by a combination of liquid and solid state {sup 15}N NMR. In the absence of catalysts, aniline undergoes a complex series of nucleophilic addition reactions with the carbonyl functionality of the humic substances to form both heterocyclic and nonheterocyclic condensation products. In the presence of the catalysts, aniline undergoes free radical coupling reactions together with nucleophilic addition reactions with the humic substances. Reaction of aniline with the whole soil most closely resembled the noncatalyzed reactions with the humic substances, as determined by solid state {sup 15}N NMR.

• OSTI ID: 214886
• Report Number(s): CONF-950801--
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
54 ENVIRONMENTAL SCIENCES
66 PHYSICS
AFFINITY
AMINES
ANILINE
AROMATICS
BINDING ENERGY
CHEMICAL REACTIONS
ENVIRONMENTAL TRANSPORT
FULVIC ACIDS
HUMIC ACIDS
LABELLED COMPOUNDS
NITROGEN 15
NMR SPECTRA
ORGANIC MATTER
POLLUTANTS
SILT
SOILS