Phenolic antioxidants inhibit the triplet-induced transformation of anilines and sulfonamide antibiotics in aqueous solution

Jannis Wenk, Silvio Canonica

Research output: Contribution to journalArticle

93 Citations (Scopus)
106 Downloads (Pure)

Abstract

Recent studies have shown that dissolved organic matter (DOM) may inhibit the excited triplet-induced oxidation of several aromatic water contaminants, in particular those containing an aniline functionality. Such an inhibition was ascribed to antioxidant moieties of DOM. The present study was conducted with the aim of verifying whether well-defined antioxidants could act as inhibitors in analogy to DOM. Various substituted phenols exhibiting antioxidant character were able, at micromolar concentration, to slow down the photoinduced depletion of several anilines and sulfonamides in aerated aqueous solution containing 2-acetonaphthone as the photosensitizer. A concomitant accelerated degradation of the phenols in the presence of such contaminants was observed. This reinforces the hypothesis of reduction of oxidation intermediates of the contaminants by the phenols. Phenol (unsubstituted) was found to be a useful inhibitor even in the case of DOM-photosensitized transformations. Phenolic antioxidants are proposed as diagnostic tools to investigate the aquatic photochemistry of aromatic amines.

Original languageEnglish
Pages (from-to)5455-5462
Number of pages8
JournalEnvironmental Science and Technology
Volume46
Issue number10
DOIs
Publication statusPublished - 15 May 2012

Fingerprint

Aniline Compounds
Sulfonamides
dissolved organic matter
antibiotics
Biological materials
antioxidant
phenol
Phenols
aqueous solution
Antioxidants
Anti-Bacterial Agents
Impurities
pollutant
inhibitor
oxidation
Oxidation
Photosensitizing Agents
Photochemical reactions
photochemistry
Phenol

Cite this

Phenolic antioxidants inhibit the triplet-induced transformation of anilines and sulfonamide antibiotics in aqueous solution. / Wenk, Jannis; Canonica, Silvio.

In: Environmental Science and Technology, Vol. 46, No. 10, 15.05.2012, p. 5455-5462.

Research output: Contribution to journalArticle

@article{08dc0cdd5e6248b8be1aeaed96214106,
title = "Phenolic antioxidants inhibit the triplet-induced transformation of anilines and sulfonamide antibiotics in aqueous solution",
abstract = "Recent studies have shown that dissolved organic matter (DOM) may inhibit the excited triplet-induced oxidation of several aromatic water contaminants, in particular those containing an aniline functionality. Such an inhibition was ascribed to antioxidant moieties of DOM. The present study was conducted with the aim of verifying whether well-defined antioxidants could act as inhibitors in analogy to DOM. Various substituted phenols exhibiting antioxidant character were able, at micromolar concentration, to slow down the photoinduced depletion of several anilines and sulfonamides in aerated aqueous solution containing 2-acetonaphthone as the photosensitizer. A concomitant accelerated degradation of the phenols in the presence of such contaminants was observed. This reinforces the hypothesis of reduction of oxidation intermediates of the contaminants by the phenols. Phenol (unsubstituted) was found to be a useful inhibitor even in the case of DOM-photosensitized transformations. Phenolic antioxidants are proposed as diagnostic tools to investigate the aquatic photochemistry of aromatic amines.",
author = "Jannis Wenk and Silvio Canonica",
year = "2012",
month = "5",
day = "15",
doi = "10.1021/es300485u",
language = "English",
volume = "46",
pages = "5455--5462",
journal = "Environmental Science & Technology",
issn = "0013-936X",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - Phenolic antioxidants inhibit the triplet-induced transformation of anilines and sulfonamide antibiotics in aqueous solution

AU - Wenk, Jannis

AU - Canonica, Silvio

PY - 2012/5/15

Y1 - 2012/5/15

N2 - Recent studies have shown that dissolved organic matter (DOM) may inhibit the excited triplet-induced oxidation of several aromatic water contaminants, in particular those containing an aniline functionality. Such an inhibition was ascribed to antioxidant moieties of DOM. The present study was conducted with the aim of verifying whether well-defined antioxidants could act as inhibitors in analogy to DOM. Various substituted phenols exhibiting antioxidant character were able, at micromolar concentration, to slow down the photoinduced depletion of several anilines and sulfonamides in aerated aqueous solution containing 2-acetonaphthone as the photosensitizer. A concomitant accelerated degradation of the phenols in the presence of such contaminants was observed. This reinforces the hypothesis of reduction of oxidation intermediates of the contaminants by the phenols. Phenol (unsubstituted) was found to be a useful inhibitor even in the case of DOM-photosensitized transformations. Phenolic antioxidants are proposed as diagnostic tools to investigate the aquatic photochemistry of aromatic amines.

AB - Recent studies have shown that dissolved organic matter (DOM) may inhibit the excited triplet-induced oxidation of several aromatic water contaminants, in particular those containing an aniline functionality. Such an inhibition was ascribed to antioxidant moieties of DOM. The present study was conducted with the aim of verifying whether well-defined antioxidants could act as inhibitors in analogy to DOM. Various substituted phenols exhibiting antioxidant character were able, at micromolar concentration, to slow down the photoinduced depletion of several anilines and sulfonamides in aerated aqueous solution containing 2-acetonaphthone as the photosensitizer. A concomitant accelerated degradation of the phenols in the presence of such contaminants was observed. This reinforces the hypothesis of reduction of oxidation intermediates of the contaminants by the phenols. Phenol (unsubstituted) was found to be a useful inhibitor even in the case of DOM-photosensitized transformations. Phenolic antioxidants are proposed as diagnostic tools to investigate the aquatic photochemistry of aromatic amines.

UR - http://www.scopus.com/inward/record.url?scp=84861121093&partnerID=8YFLogxK

UR - http://dx.doi.org/10.1021/es300485u

U2 - 10.1021/es300485u

DO - 10.1021/es300485u

M3 - Article

VL - 46

SP - 5455

EP - 5462

JO - Environmental Science & Technology

JF - Environmental Science & Technology

SN - 0013-936X

IS - 10

ER -