Mechanisms of Diazo Coupling Reactions. Part XXX. N-Diazo Coupling of p-Chloroaniline in Acetonitrile: Rate-Limiting Proton Transfer

Article abstract of DOI:10.1002/hlca.19810640602

The N-diazo coupling of p-chloroaniline with p-chlorobenzenediazonium tetrafluoroborate in acetonitrile at 30 deg shows non-linear base catalysis by water.The results are interpreted in terms of the S_E2 mechanism with rate-limiting proton loss at low base concentration; it is postulated, moreover that the reaction proceeds via transition states in which varying degrees of H-bonding from the amine and the intermediate ?-complex to different water species influence the initial step and the base catalysis.