Synthesis, Structure, and Chemical Properties of 1-Oxidopyridinediazonium Sulfonates = Синтез, структура и химические свойства 1-оксидопиридиндиазоний сульфонатов / E. A. Krasnokutskaya, A. N. Sanzhiev, K. D. Erin [et al.]
Set Level: Russian Journal of Organic Chemistry, Журнал органической химии, New York, Springer Science+Business Media LLC.Language: английский.Country: США.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.Bibliography: References: 33 tit.Subject: aminopyridine 1-oxides | diazotization | 1-oxidopyridinediazonium sulfonates | электронный ресурс | труды учёных ТПУ Online Resources:https://doi.org/10.1134/S1070428024603029 | Статья на русском языкеTitle screen
References: 33 tit
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
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