Acidity functions and the protonation of weak bases. Part VII. The protonation behaviour of dimethylaminopyridines and their N-oxides
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 671-673
- https://doi.org/10.1039/p29720000671
Abstract
The first and second pKa values for the title compounds and some nitro-substituted derivatives are reported. First protonation occurs in all cases on the ring nitrogen (pyridines) or at the N-oxide oxygen (N-oxides), and the pKa values are in line with predictions from the Hammett equation. The second protonation at the NMe2 group follows the H0‴ acidity function, and thermodynamic second pKa values calculated using the slope m of [BH+]/[B]vs. H0 are also well correlated by the Hammett equation.Keywords
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