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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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Acid–Base Equilibria: Quantitative Treatment

Acid–Base Equilibria: Quantitative Treatment

(p.10) 2 Acid–Base Equilibria: Quantitative Treatment
Acids and Bases

Brian G. Cox

Oxford University Press

Quantitative treatment of acid–base behaviour is presented, including the definition of acids, bases, and dissociation constants, and the important relationships between solution pH, acid strength, acid–base ratios, and species distribution. Molecular structural features of acids, which influence both the acid strengths and their dependence upon solvent, are summarized. They include the bond strength, the ability to stabilize anions and cations by charge dispersion, and the nature of the atom to which the proton is bonded. The acidity of carbon acids, which are widely used in synthetic procedures, is reviewed. Structural rearrangements on ionization of ketones, esters, and nitroalkanes, which allow the negative charge generated on ionization of the C-H bond to reside on oxygen, leads to greatly enhanced acidity. The inductive influence of strongly electron-withdrawing groups ? to the ionizing C-H bond is important for nitriles and sulphones.

Keywords:   dissociation constant, pKa, species distribution, zwitter-ion, charge dispersion, carbon acids, ketones, nitroalkanes

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