Abstract
The (OHO) +-type cationic heteroconjugation equilibria have been studied in systems consisting of substituted pyridine N-oxides and trimethylamine N-oxide in the polar protophobic aprotic solvent, propylene carbonate. The highest values of heteroconjugation constants, log K BHBl + , oscillating around the value equal to 4, were obtained in systems where both the proton donor and proton acceptor had comparable basicities. A comparison of the cationic heteroconjugation constants determined in propylene carbonate with those determined in the less polar acetonitrile led to the conclusion that the increased polarity of the aprotic solvent enhanced the tendency towards cationic heteroconjugation.
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