Related Experiment Video
Updated: Feb 18, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Photooxidation of Aniline Derivatives Can Be Activated by Freezing Their Aqueous Solutions
Pablo Corrochano1, Dana Nachtigallová2, Petr Klán1,3
1RECETOX, Faculty of Science, Masaryk University , Kamenice 5, 62500 Brno, Czech Republic.
Abstract:
A combined experimental and computational approach was used to investigate the spectroscopic properties of three different aniline derivatives (aniline, N,N-dimethylaniline, and N,N-diethylaniline) in aqueous solutions and at the air-ice interface in the temperature range of 243-298 K. The absorption and diffuse reflectance spectra of ice samples prepared by different techniques, such as slow or shock freezing of the aqueous solutions or vapor deposition on ice grains, exhibited unequivocal bathochromic shifts of 10-15 nm of the absorption maxima of anilines in frozen samples compared to those in liquid aqueous solutions. DFT and SCS-ADC(2) calculations showed that contaminant-contaminant and contaminant-ice interactions are responsible for these shifts. Finally, we demonstrate that irradiation of anilines in the presence of a hydrogen peroxide/O2 system by wavelengths that overlap only with the red-shifted absorption tails of anilines in frozen samples (while having a marginal overlap with their spectra in liquid solutions) can almost exclusively trigger a photochemical oxidation process. Mechanistic and environmental considerations are discussed.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Oxidations of Aldehydes and Ketones to Carboxylic Acids
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
Preparation of Amines: Reduction of Amides and Nitriles
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
Diazonium Group Substitution: –OH and –H