Версия от 17:47, 21 марта 2024; EducationBot(обсуждение | вклад)(Новая страница: «{{Английская Википедия/Панель перехода}} {{Short description|Chemical test to distinguish primary, secondary & tertiary amines}} The '''Hinsberg reaction''' is a chemical test for the detection of primary, secondary and tertiary amines. The reaction was first described by Oscar Hinsberg in 1890.<ref>O. Hinsberg: ''Ueber die Bildung von Säureestern und Säureamiden bei Gegenwart von Wasser und Alkali'', in: ''Ber. Dts...»)
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Шаблон:Short description
The Hinsberg reaction is a chemical test for the detection of primary, secondary and tertiary amines. The reaction was first described by Oscar Hinsberg in 1890.[1][2] In this test, the amine is shaken well with the Hinsberg reagent (benzenesulfonyl chloride) in the presence of aqueous alkali (either KOH or NaOH). A primary amine will form a soluble sulfonamide salt. Acidification of this salt then precipitates the sulfonamide of the primary amine. A secondary amine in the same reaction will directly form an insoluble sulfonamide. A tertiary amine will not react with the original reagent (benzene sulfonyl chloride) and will remain insoluble. After adding dilute acid this insoluble amine is converted to a soluble ammonium salt. In this way the reaction can distinguish between the three types of amines.[3]
Tertiary amines are able to react with benzenesulfonyl chloride under a variety of conditions; the test described above is not absolute. The Hinsberg test for amines is valid only when reaction speed, concentration, temperature, and solubility are taken into account.[4]
Reactions
Amines serve as nucleophiles in attacking the sulfonyl chloride electrophile, displacing chloride. The sulfonamides resulting from primary and secondary amines are poorly soluble and precipitate as solids from solution.
↑O. Hinsberg: Ueber die Bildung von Säureestern und Säureamiden bei Gegenwart von Wasser und Alkali, in: Ber. Dtsch. Chem. Ges.1890, 23, 2962–2965; Шаблон:Doi
↑O. Hinsberg, J. Kessler: Ueber die Trennung der primären und secundären Aminbasen, in: Ber. Dtsch. Chem. Ges.1905, 38, 906–911; Шаблон:Doi
↑"The systematic identification of organic compounds" 4th ed. by Ralph L. Shriner, Reynold C. Fuson, and David Y. Curtin. John Wiley & Sons, Inc., New York, 1956. Шаблон:Doi and more recent editions.