Kinetic study of phenol nitrosation in protic and aprotic solvents

The specific constants of the phenol nitrosation reaction were determined over a temperature range of 0°C to 40°C in the following solvents: water, ethanol, dimethylsulfoxide, acetonitrile, chloroform, benzene and cyclohexane. The influence of several strong electrolytes on the nitrosation rate in aqueous media was studied in the presence of a strong acid, 0.1 N, HCl, and without it. The magnitude of the primary isotopic effect which is produced in protic and aprotic solvents was also investigated. On the basis of an analysis of the yields and from the reaction kinetics found in this work we propose a nitrosation reaction mechanism in aprotic solvents. The nitrosonium ion plays no role in the mechanism.