Optical Generation of Hydrated Electrons from Aromatic Compounds. II<sup>1</sup>

Joschek, Hans-Ingo; Grossweiner, Leonard I.

doi:10.1021/ja00966a017

Cited by 135 publications

(43 citation statements)

References 6 publications

(6 reference statements)

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“…The first step is conversion of the carboxylate (RC(= O)O-) group to a carboxyl radical (RC(= O)O◊) by photoionization. Such a photochemically activated electron transfer is well established for a variety of substituted 2-arylacetic acids (Joschek and Grossweiner, 1966;Crosby and Tang, 1969). Decarboxylation, resulting in carbon dioxide and a benzylic radical, is then proposed to occur.…”

Section: Discussion Naproxenmentioning

confidence: 99%

Photochemical fate of pharmaceuticals in the environment: Naproxen, diclofenac, clofibric acid, and ibuprofen

Packer

Werner

Latch

et al. 2003

Aquatic Sciences - Research Across Boundaries

388

194

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The aqueous photochemistry of four pharmaceutical compounds detected in surface waters (naproxen, diclofenac, ibuprofen, and clofibric acid) was investigating in purified (Milli-Q) water and in Mississippi River water (MRW). Both direct photolysis and hydroxyl radical-mediated indirect photolysis (using a combination of probe and quencher experiments) were studied. Singlet oxygenation was also investigated for naproxen. Second-order rate constants for reaction with hydroxyl radical were determined using Fenton's reagent. Naproxen was rapidly transformed via direct photolysis in sunlight in both Milli-Q and MRW. The radical quencher isopropyl alcohol (IPA), had a similar effect in both systems, and this effect was interpreted as a reaction of a carboxyl radical intermediate of naproxen. Diclofenac Aquatic Scienceswas found to undergo rapid direct photolysis under sunlight, confirming the results of prior studies. Addition of IPA led to more rapid transformation, possibly due to formation of other radical species or photoreduction with IPA serving as the H-source. When irradiated under natural sunlight, slow direct photolysis of clofibric acid is observed in Milli-Q water, and a combination of direct photolysis and radical mediated indirect processes appear responsible for clofibric acid photolysis in MRW. The dominant photochemical loss process for ibuprofen irradiated with a medium pressure Hg-vapor lamp was identified as reaction with photo-generated radicals. These results suggest that photolytic processes are important removal mechanisms for pharmaceutical compounds discharged into sunlit surface waters.

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Section: Discussion Naproxenmentioning

confidence: 99%

Photochemical fate of pharmaceuticals in the environment: Naproxen, diclofenac, clofibric acid, and ibuprofen

Packer

Werner

Latch

et al. 2003

Aquatic Sciences - Research Across Boundaries

388

194

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“…la. The red absorption was identified with c, [3,4], which has been confirmed by quenching in the presence of…”

mentioning

confidence: 90%

The Role of the Hydrated Electron in Photoreduction of Cystine in the Presence of Indole

Grossweiner

Usui

1970

Photochem & Photobiology

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“…(49,92) The most direct evidence for the existence of this mechanism is derived from flash photolysis studies, which have shown that ultraviolet irradiation of aqueous solutions of indole and its derivatives, including tryptophan, results in formation of solvated electrons. (93,94) While accurate measurements of the quantum yield of solvated electrons will be required to assess the quantitative significance of this mechanism, there is considerable indirect evidence that it may be an important factor in the radiationless deactivation of the indole excited state. The quantum yield of indole in water is strongly temperature dependent.…”

Section: Radiationless Deactivation Of the Excited Statementioning

confidence: 99%

The Luminescence of the Aromatic Amino Acids

Weinryb

Steiner

1971

Excited States of Proteins and Nucleic Acids

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Optical Generation of Hydrated Electrons from Aromatic Compounds. II¹

Cited by 135 publications

References 6 publications

Photochemical fate of pharmaceuticals in the environment: Naproxen, diclofenac, clofibric acid, and ibuprofen

Photochemical fate of pharmaceuticals in the environment: Naproxen, diclofenac, clofibric acid, and ibuprofen

The Role of the Hydrated Electron in Photoreduction of Cystine in the Presence of Indole

The Luminescence of the Aromatic Amino Acids

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Optical Generation of Hydrated Electrons from Aromatic Compounds. II1

Cited by 135 publications

References 6 publications

Photochemical fate of pharmaceuticals in the environment: Naproxen, diclofenac, clofibric acid, and ibuprofen

Photochemical fate of pharmaceuticals in the environment: Naproxen, diclofenac, clofibric acid, and ibuprofen

The Role of the Hydrated Electron in Photoreduction of Cystine in the Presence of Indole

The Luminescence of the Aromatic Amino Acids

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Optical Generation of Hydrated Electrons from Aromatic Compounds. II¹