Predicting the pKa Values of the Deprotonation Equilibria of Benzenonium Carbocations
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Geelan, David
Jagannadham, V
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Abstract
The pKa(H) value of the benzenonium carbocation (C6H7+, cy-clohexadienyl cation, Wheland intermediate) is −24.3 [1]. The Hammett’s reaction constant (ρ) value for the deprotonation equilibrium is 14.3 [2]. {fx283-01} Using this value, the Hammett substituent constant, (σX) of any substituent (X) and the Hammett equation, pKH − pKX = ρσ, the pKa(X) values of any meta or para-substituted benzenonium carbocation deprotonation equilibria can be estimated.
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Resonance
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27
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2
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Social Sciences
Education, Scientific Disciplines
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pK(a) values
Hammett equation
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Sanjeeva, R; Geelan, D; Jagannadham, V, Predicting the pKa Values of the Deprotonation Equilibria of Benzenonium Carbocations, Resonance, 2022, 27 (2), pp. 283-288