Why is pyridine so much more acidic than other similar imines (5.5 versus ~9, see picture)? Wouldn't delocalization of the positive charge into the aromatic system stabilize it and hence decrease acidity? Also the lone pair of pyridine is not delocalized into the perpendicular $\pi$-system and hence not any less available than the one of the projected imine.
(Source: Organic Chemistry by Clayden et al. p. 1149. )
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