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Equilibrium Constants for Ionisation and Enolisation of 3-Nitrobutan-2-one

✍ Scribed by Antonella Fontana; Paolo De Maria; Gabriella Siani; Marco Pierini; Simona Cerritelli; Roberto Ballini

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 307 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200004)2000:8<1641::aid-ejoc1641>3.0.co;2-5

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✦ Synopsis

The equilibrium constant for the keto-enol tautomerism of 3nitrobutan-2-one K T = [enol]/[ketone] has been measured in water as 4.57 ϫ 10 -3 (pK T = 2.34) by combining the rate constants for ketonisation of the enolate form and pK a of the ketone at 25 °C. The rates of ketonisation were measured by a rapid kinetic technique and the pK a was determined spectrophotometrically and potentiometrically as 5.15. A comparison with 2-butanone and acetone shows a strong influence of the nitro group in enhancing the acidity of the substrate and in

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