Dediazoniation of p-hydroxy and p-nitrobenzenediazonium ions in an aqueous medium: Interference by the chelating agent diethylenetriaminepentaacetic acid

Abstract

We have made a comparative study of the dediazoniation of p-hydroxy and p-nitrobenzenediazonium ions. The electron-withdrawing and donating properties of the -NO2 and -OH groups strongly determine the reactivity of both compounds, thus exerting different influences upon the dediazoniation reaction. We describe here how the decomposition of p-hydroxy and p-nitrobenzenediazonium ions in a neutral aqueous medium follows a different pattern in the presence of the metal-chelator diethylenetriaminepentaacetic acid (DTPA). The decomposition rate of p-hydroxybenzene diazonium decreases whilst the decomposition of the p-nitrobenzenediazonium ion is enhanced. The experimental data are discussed with reference to a common scheme of interference for both benzenediazonium ions in the light of the radical-scavenging capacity of DTPA.Key words: p-hydroxybenzenediazonium ion, p-nitrobenzenediazonium ion, di-ethylenetriaminepentaacetic acid, dediazoniation, radical scavenging, artifacts.