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Hammett equation is applied and the magnitude of substituent effect in terms of Hammett r has been estimated for the deprotonation equilibriums of highly unstable arenium ions (Wheland intermediates) XC6 H6 + XC6 H5 + H+ based on the attenuation effect of methylene group on the dissociation equilibriums of anilinium ions, benzyl ammonium ions and 2-phenylethyl ammonium ions. The Hammett r was found to be 14.3. The Hammett r for the deprotonation equilibriums of pyridinium ions XC5H4NH + XC5H4N +H+ was estimated from the plot of log Ka vs Hammett s, this value is 5.90. The magnitude of substituent effect in terms of Taft r* has been estimated for the deprotonation equilibriums of methanium ions RCH4 + RCH3 + H+ based on the attenuation effect of methylene group on the dissociation equilibriums of aliphatic amines and was found to be 6.9. The Taft r* for the deprotonation equilibriums of alkyl ammonium ions RNH3 + RNH2 + H + was estimated from the plot of log Ka vs Taft s*, this value is 3.28. The large differences in the Hammett r of 8 units when carbon is replaced with nitrogen as heteroatom in the six-member aromatic ring and 3.6 units of Taft r* when carbon is replaced with nitrogen in aliphatic derivatives respectively is explained.

Tetrahedral Nature Determines the Stability of Reactive Intermediates: A Chemical Education Perspective