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Acids and BasesSolvent Effects on Acid-Base Strength$
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Brian G. Cox

Print publication date: 2013

Print ISBN-13: 9780199670512

Published to Oxford Scholarship Online: May 2013

DOI: 10.1093/acprof:oso/9780199670512.001.0001

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High-Basicity Polar Aprotic Solvents

High-Basicity Polar Aprotic Solvents

(p.76) 6 High-Basicity Polar Aprotic Solvents
Acids and Bases

Brian G. Cox

Oxford University Press

Basic polar aprotic solvents such as dimethylsulphoxide, dimethylformamide, and N-methylpyrrolidin-2-one are very poor at solvating anions, but interact strongly with cations and the proton in particular. Their low autoionization constants are compatible with the use of very strong bases, thus allowing direct measurement of dissociation constants for an extensive range of weak acids: ketones, esters, nitroalkanes, nitriles, amides, anilines, and alcohols. Poor anion solvation results in dissociation constants of carboxylic acids and phenols that are typically several orders of magnitude lower than in water, and show much greater sensitivity to substituents. Extensive homohydrogen-bond formation is also observed for carboxylic acids and phenols. Protonated nitrogen bases show slightly higher acidities relative to those in water. Excellent correlations exist for pKa-values amongst the solvents and with aqueous values.

Keywords:   dimethylsulphoxide, dimethylformamide, dimethylacetamide, n-methylpyrrolidin-2-one, liquid ammonia, carboxylic acids, phenols, amines, carbon acids, amino-acids, homohydrogen-bonds

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