Synthesis, Structure, and Chemical Properties of 1-Oxidopyridinediazonium Sulfonates
| Parent link: | Russian Journal of Organic Chemistry=Журнал органической химии.— .— New York: Springer Science+Business Media LLC. Vol. 61, No. 1.— 2025.— P. 60-72 |
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| Další autoři: | , , , , , |
| Shrnutí: | Title screen 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 Текстовый файл AM_Agreement |
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2025
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| On-line přístup: | https://doi.org/10.1134/S1070428024603029 Статья на русском языке |
| Médium: | Elektronický zdroj Kapitola |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=680734 |
| Shrnutí: | Title screen 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 Текстовый файл AM_Agreement |
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| DOI: | 10.1134/S1070428024603029 |