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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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(p.1) 1 Introduction
Acids and Bases

Brian G. Cox

Oxford University Press

Non-aqueous solvents typically lack water’s ability to solvate effectively both anions and cations, and consequently have acidity scales that differ considerably from those in water. These differences often lead to profound changes in the available range and reactivity of acids and particularly bases, which has important consequences in synthetic and analytical chemistry and in the formation and isolation of salts. Properties of solvents are reviewed. The presence (protic solvents) of absence (aprotic solvents) of acidic protons capable of hydrogen-bond donation is a key distinguishing feature of solvents. Important also is the ability to stabilize charged species through donation or acceptance of electron pairs, as represented by parameters such as solvent Donor Numbers, Acceptor Numbers, and hydrogen-bond basicity. The dielectric constant is strongly influential in determining the extent of ion-association, which is a dominant factor in acid–base equilibria in low-dielectric media.

Keywords:   protic solvents, aprotic solvents, dielectric constant, donor numbers, acceptor numbers, crystallization

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