
AbstractThe adicity of methyl bonded to pyridine nucleus of the s‐collidine depends on the solvent and the counterion nature. With Li+ or Na+ cations in Et2O, we have observed the decreasing acidity order: NH3 > Me‐2 > o‐tolunitrile > Me‐4; with Li+ or Na+ in liquid NH3: o‐tolunitrile > Me‐4 > NH3 > Me‐2. On the other hand, with K+ in Et2O or in liquid NH3: Me‐4 Me‐2 > NH3. An estimate for the pKa value of the s‐collidine (4‐methyl group) is ∼︁∼29 at –33°C in liquid NH3, with Na+ as counterion.
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