Synthesis of stable diazonium sulfonates and their chemical properties in pyridine derivatives suggests implications for future reactions.
The products of diazotization of 2-, 3-, and 4-aminopyridin-1-oxides in the presence of TsOH, TfOH, and camphorsulfonic acid were investigated by IR, NMR, X-ray diffraction analysis, ESI/MS and MS2 spectroscopy, and B3LYP/aug-cc-pVDZ. The structures of the products and their stability during storage depend on the type of the starting aminopyridine. 4-Aminopyridin-1-oxide reacts to give stable diazonium sulfonates, and the 2-aminoisomer gives [1,2,3,5]oxotriazol[5,4-a]pyridinium-2 sulfonates. All products readily undergo reactions typical for diazonium salts. By the B3LYP/aug-cc-pVDZ method it was determined that 4-diazonium-pyridinium-1-oxide and benzoldiazonium cation have the highest stability in the series of diazonium cations of pyridine, pyridine-1-oxide and benzoldiazonium cation.
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E. A. Krasnokutskaya (2025) studied this question.
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