The Wallach rearrangement. Part V. Acid catalyzed hydrolysis of azobenzene-4-hydrogen sulfate

Autor:	E. Buncel, W. M. J. Strachan
Rok vydání:	1969
Předmět:	chemistry.chemical_classification Potassium Organic Chemistry Salt (chemistry) chemistry.chemical_element General Chemistry Wallach rearrangement Catalysis chemistry.chemical_compound Hydrolysis Azobenzene chemistry Hydrogen Sulfate Acid catalyzed Polymer chemistry Organic chemistry Sulfate
Zdroj:	Canadian Journal of Chemistry. 47:911-917
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v69-149
Popis:	In relation to the intermediacy of azobenzene-4-hydrogen sulfate in the Wallach rearrangement of azoxybenzene, the potassium salt has been characterized and subjected to examination under acidic conditions. A pKa value of −2.14 has been obtained, for N-protonation. The sulfate salt hydrolyzes to p-hydroxyazobenzene in acid media and the rate of the reaction has been measured over the region 22–42% H2SO4 at 25° spectrophotometrically. A correlation between rate and acidity function indicates that a two-proton process is involved; a reactive species is proposed having a nitrogen and the phenolic oxygen protonated. The relevance of these findings to Wallach rearrangement studies is discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::85dd7f06111bb5c0150f00a3c9d52b33 https://doi.org/10.1139/v69-149 Zobrazit plný text záznamu