Conversion of o-hydroxyaldehydes and ketones into o-hydroxyanilides by monochloramine

Crochet, Roy A.; Kovacic, Peter

doi:10.1039/c39730000716

Cited by 8 publications

(4 citation statements)

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“…In addition, the effects of 4-aminophenol and salicylate association derivatives on lipid peroxidation inhibition in the concentration of 1 mM in human erythrocytes were examined using the TBARS assay ( Figure 5), in accordance with the method reported previously (6,18,19). The antioxidant efficiency of the three phenolic drugs against lipid peroxidation in an iron dependent system, initiated by Fe 2+ ⁄ ascorbato and formation of lipid peroxides, was sig- nificantly inhibited by the test compounds (S5-S7).…”

Section: Determination Of the Inhibition Of Lipid Peroxidation In Hummentioning

confidence: 77%

“…Structures were confirmed with nuclear magnetic resonance and melting point (18,19). With thin layer chromatography (TLC), each isolated product gave a single spot.…”

Section: Chemistrymentioning

confidence: 95%

“…With thin layer chromatography (TLC), each isolated product gave a single spot. Structures were confirmed with nuclear magnetic resonance and melting point (18,19). Solutions of metal ions were prepared from their chloride salts in HPLC grade water.…”

Section: Chemistrymentioning

confidence: 99%

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Design and Evaluation of 4‐Aminophenol and Salicylate Derivatives as Free‐Radical Scavenger

et al. 2013

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This theoretical and experimental study describes the design and evaluation of the free-radical scavenging effect for the molecular association of 4-aminophenol and salicylate derivatives. For this purpose, we employed theoretical methods for the selection of antioxidant drugs and the rapid methods of evaluation: the 1,1-diphenyl-2-picrylhydrazyl radical and the thiobarbituric acid reactive substances in the lipid peroxidation initiated by Fe(2+) and ascorbic acid in human erythrocytes. The associate derivatives exhibited a more potent inhibition than the salicylic acid, while the benzoyl compound exhibited a more potent inhibition than paracetamol. The molecular parameters related to the electron distribution and structure (ionization potential and energy of the highest occupied molecular orbital) correlated very well with the antioxidant action of the compounds studied here in different tests.

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Section: Determination Of the Inhibition Of Lipid Peroxidation In Hummentioning

confidence: 77%

“…Structures were confirmed with nuclear magnetic resonance and melting point (18,19). With thin layer chromatography (TLC), each isolated product gave a single spot.…”

Section: Chemistrymentioning

confidence: 95%

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Design and Evaluation of 4‐Aminophenol and Salicylate Derivatives as Free‐Radical Scavenger

et al. 2013

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“…Aldehydes and ketones produce amides or chloroimines when treated with monochloramine (20,21). Chloroimines derived from aldehydes can produce nitriles, probably by undergoing dehydrohalogenation (21).…”

Section: Reactions Of Oxidants/disinfectants With Organic Aliphatic Smentioning

confidence: 99%

Occurrence of by-products of strong oxidants reacting with drinking water contaminants--scope of the problem.

Rice¹,

Gomez-Taylor²

1986

Environ Health Perspect

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This paper describes results of a detailed literature review of the organic and inorganic by-products that have been identified as being formed in aqueous solution with four of the strong oxidizing/disinfecting agents commonly employed in drinking water treatment. These agents are: chlorine, chlorine dioxide, chloramine, and ozone. Significant findings include the production of similar nonchlorinated organic oxidation products from chlorine, chlorine dioxide, and ozone. In addition, all three chlorinous oxidants/disinfectants can produce chlorinated by-products under certain conditions. The presence of chloronitrile compounds in drinking waters is indicated to arise from reactions of chlorine or chloramine to amine/amide functions in amino acids or proteinaceous materials, followed by dehydrohalogenation. These nitriles could hydrolyze to produce the corresponding chloroacetic acids. It is concluded that to minimize the presence of oxidation by-products in drinking waters, the concentrations of oxidizable organic/inorganic impurities should be lowered before any oxidizing agent is added.

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Chloramine

Goehring¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Conversion of o-hydroxyaldehydes and ketones into o-hydroxyanilides by monochloramine

Cited by 8 publications

References 0 publications

Design and Evaluation of 4‐Aminophenol and Salicylate Derivatives as Free‐Radical Scavenger

Design and Evaluation of 4‐Aminophenol and Salicylate Derivatives as Free‐Radical Scavenger

Occurrence of by-products of strong oxidants reacting with drinking water contaminants--scope of the problem.

Chloramine

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