Abstract
Radziszewski amidation, namely the peroxide-mediated conversion of nitriles into amides, is a chemiluminescent reaction involving singlet oxygen. Its increasing relevance in green chemistry and analytical chemistry makes it an important subject to be discussed in advanced chemistry courses. To turn the attention of lecturers, teachers, and students toward this reaction, the history of its discovery as well as its practical applications is discussed. Moreover, a simple and effective experiment to demonstrate the chemiluminescent properties of Radziszewski amidation is provided.
Highlights
The amide functional group is widespread in nature and of fundamental importance in chemistry, as it determines the physicochemical properties of countless biological as well as artificial molecules
The addition of 10 mM ascorbic acid completely quenches the chemiluminescence, but this cannot be considered as crucial evidence of singlet oxygen formation as ascorbic acid is a generic scavenger of radicals and reactive oxygen species.[32]
Furfuryl alcohol is a renowned specific scavenger of singlet oxygen, with which it can react generating a mixture of oxidation products, whose nature and relative yields vary with respect to the solvent employed: Scheme 1 shows the structures of the products that, according to the literature, are expected to form in aqueous solution.[33]
Summary
The amide functional group is widespread in nature and of fundamental importance in chemistry, as it determines the physicochemical properties of countless biological as well as artificial molecules. In the 1950s, as he was studying the reaction of benzonitrile with mildly alkaline hydrogen peroxide,[4,5] found that the rate-determining step was the reaction of hydroperoxide HOO− with the carbon atom of the nitrile group to give a reactive intermediate, peroxycarboximidic acid (eq 2). The latter would oxidize another molecule of hydrogen peroxide by a successive fast reaction, producing the amide (eq 3). A brighter light, clearly visible by the naked eye, can be obtained by the addition of luminol
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
