The oxidation of 3-aminophthalhydrazide ("luminol") as a lecture demonstration of chemiluminescence

Abstract

Attention is directed to the most striking instance of chemiluminescence which appears to have been observed and to the extraordinary advantages which the reaction possesses over the conventional cases. A simple economical two-stage synthesis of 3-aminophthalhydrazide is described which readily gives excellent yields of pure product. Specific directions are given for demonstration of its brilliant chemiluminescence in dilute aqueous alkaline oxidizing agents. THE STUDY of chemical reactions in which visible light is evolved at ordinary or low temperatures has largely been left to physics, physical chemistry, or biochemistry. Nevertheless, countless instances of such development of visible radiation are on record and many (if not most) involve organic compounds. However, in the vast majority of cases either the amount of light evolved is not impressive, or the reaction is brought about only under inconvenient conditions, or the substances involved are expensive or difficultly accessible. Partly for these reasons general attention to the matter has been but occasional and the most impressive and convenient illustration of the phenomenon appears to have been largely overlooked.Most chemiluminescent reactions are oxidations.Extensive resumes of hundreds of individual cases are already available.1 Of the many instances of organic compounds of known structure given in these references there appears to be a small group which gives a maximum of visible light. This group includes the following:(1) various reactions of Grignard compounds, such as the Wedekind2 reaction between chloropicrin and phenylmagnesium bromide in ether solution, the reaction of Grignard compounds with other nitro compounds,3 or the oxidation of various Grignard * Contribution No.

The free heme concentration in healthy human erythrocytes

“…Reaction (1c) is accompanied by luminescence at 428 nm [27,28]. The luminescence intensity is proportional to the rate of catalytic decomposition of peroxide.…”

“…The transformation of the analyte to a catalyst of a reaction with a well-detectable product underlies the high sensitivity of this method. Furthermore, the luminol reaction is an example of very strong chemiluminescence [27,28]. The strong amplification of the signal allows detection and quantification of hematin or hemin levels as low as 50 pM, see tests of sensitivity below.…”

Thermodynamic mechanism of free heme action on sickle cell hemoglobin polymerization

“…Reaction (1c) is accompanied by luminescence at 428 nm . The luminescence intensity is proportional to the rate of catalytic decomposition of peroxide.…”

“…The transformation of the analyte to a catalyst of a reaction with a well detectable product underlies the high sensitivity of this method. Furthermore, the luminol reaction is an example of very strong chemiluminescence . The strong amplification of the signal allows detection and quantification of hematin levels as low as 50 pM.…”

Microwave Preparation of Ag Nanoparticles for Chemiluminescence Enhancement

“…It has been long known that when this excited state relaxes to its ground state, a blue photon is emitted. 11 Trace amounts of Fe, Cu, Ag, Co or [Fe(CN) 3 ] 3+ species catalyze this reaction by increasing the rate of H 2 O 2 decomposition. 12 In particular, Ag NPs are known to catalyze this decomposition into strongly oxidizing species (hydroxyl radicals and superoxide anions) that react with luminol emitting a large amount of photons.…”