Solvent effect on transformations of triazenes as studied by means of physical chemistry and quantum chemical calculations

We found that triazenes can undergo heterolytic transformations in the presence of diazonium cations, in particular, in the hydrophilic organic solvents. This effect depends on the nature of the solvents (i.e., protic or aprotic). It was proved by the methods of high performance liquid chromatography, spectrophotometry, and quantum-chemical calculations of model systems. Our work demonstrated a correlation between the inductive constant of substitutive in azo-component and the yield of reaction product, namely triazene of 4 nitroaniline (1,3-bis-(4-nitrobenzene)-triazene). We have proposed a mechanism of the transformations of these triazenes.