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Steric Effects on the Proton-Transfer Equilibria of Ketones, Sulfoxides, and Phenols

✍ Scribed by Alessandro Bagno; Renato L. Boso; Nicola Ferrari; Gianfranco Scorrano

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 357 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199907)1999:7<1507::aid-ejoc1507>3.0.co;2-j

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✦ Synopsis

The proton-transfer equilibrium of several bases and acids, having a sterically hindered basic or acidic site. Thus, it is demonstrated that the anomalously low basicity of two including some sterically hindered ketones, sulfoxides, and phenols, has been investigated by means of the sterically hindered ketones (tBu 2 CO and PhCOtBu) is enthalpic in origin and stems from steric hindrance to the determination of the thermodynamics of the equilibrium, NMR 13 C relaxation measurements, and quantum chemical solvation of their protonated forms. No such effect is found for analogous sulfoxides, whereas phenols display a more calculations. The analysis of such data yields information about the steric effects on basicity or acidity and about the complex behavior. underlying reasons for the anomalous behavior of species Table 1. Thermodynamic parameters for the ionization at 25°C of molecules, as confirmed by NMR relaxation measure-E-mail

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