Author:
Nicholas A. Martin de P.,Arnold Donald R.
Abstract
Three methods for estimating the pKa of a radical cation using thermochemical cycles are discussed. These methods enable the calculations of the pKa of radical cations which have not been determined experimentally. Radical cation acids are classified according to the nature of their respective conjugate bases. The application of these methods is illustrated for a σ-acid (the benzene radical cation) and π-acid (the toluene radical cation). The potential of these methods to estimate relative and absolute solvation energies is also discussed. The use of thermochemical cycles in estimating standard oxidation potentials of organic compounds is outlined.Calculations show that the toluene radical cation is an extremely strong acid and the benzene radical cation a moderately strong acid in acetonitrile solution. Difficulties in directly determining the pKa value of aromatic hydrocarbon radical cations are also discussed.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
259 articles.
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