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Abstract <p>The diazotization products of 2-, 3- and 4-aminopyridine 1-oxides in the presence of <i>p</i>-toluene­sulfonic acid, trifluoromethanesulfonic acid, and camphorsulfonic acid have been studied by IR and NMR spectroscopy, X-ray analysis, ESI mass spectrometry (MS and MS2), and B3LYP/aug-cc-pVDZ quantum chemical calculations. The product structure and their storage stability depend on the initial aminopyridine <i>N</i>-oxide. 4-Aminopyridine 1-oxide gives rise to stable diazonium sulfonate, whereas 2-aminopyridine 1-oxide is converted to [1,2,3,5]oxatriazolo[5,4-<i>a</i>]pyridin-4-ium sulfonates. All diazotization products easily undergo transformations typical of diazonium salts. According to the B3LYP/aug-cc-pVDZ calculations, 1-oxido­pyridine-4-diazonium cation is the most stable in the series of diazonium ions derived from aminopyridines and aminopyridine 1-oxides and benzenediazonium ion.</p>

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Synthesis, Structure, and Chemical Properties of 1-Oxidopyridinediazonium Sulfonates

  • 期刊论文

  • 发表日期：

    2025年1月1日

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  • E. A. Krasnokutskaya,
  • A. N. Sanzhiev,
  • K. D. Erin,
  • A. A. Bondarev,
  • A. S. Potapov,
  • V. D. Filimonov

摘要

Abstract

The diazotization products of 2-, 3- and 4-aminopyridine 1-oxides in the presence of p-toluene­sulfonic acid, trifluoromethanesulfonic acid, and camphorsulfonic acid have been studied by IR and NMR spectroscopy, X-ray analysis, ESI mass spectrometry (MS and MS2), and B3LYP/aug-cc-pVDZ quantum chemical calculations. The product structure and their storage stability depend on the initial aminopyridine N-oxide. 4-Aminopyridine 1-oxide gives rise to stable diazonium sulfonate, whereas 2-aminopyridine 1-oxide is converted to [1,2,3,5]oxatriazolo[5,4-a]pyridin-4-ium sulfonates. All diazotization products easily undergo transformations typical of diazonium salts. According to the B3LYP/aug-cc-pVDZ calculations, 1-oxido­pyridine-4-diazonium cation is the most stable in the series of diazonium ions derived from aminopyridines and aminopyridine 1-oxides and benzenediazonium ion.