The pKa values of 23 pyridinium ions have been calculated by observing the change in the n.m.r. chemical shift on deprotonation. The values for ΔG, ΔH, and ΔS have been obtained for this deprotonation from the pKa values at more than one temperature. The Hammett plot of the ionization values indicates that the pKa of a substituted pyridine can be estimated by the equation pKa= 5·35 –5·23∑σ.
M. R. Chakrabarty, C. S. Handloser and M. W. Mosher, J. Chem. Soc., Perkin Trans. 2, 1973, 938 DOI: 10.1039/P29730000938
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