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Communication | Regular issue | Vol 26, No. 12, 1987, pp.3071-3075
Published online, 1st January, 1970
DOI: 10.3987/R-1987-12-3071
Reversible Formation of a Pseudobase from 1-Methylpyridinium-3-carb(ox)aldehyde

James F. Rusling and Petr Zuman

*Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, U.S.A.

Abstract

The geminal diol anion of 1-methylpyridinium-3-carb(ox)aldehyde hydrate in aqueous alkaline solutions forms an unstable pseudobase by nucleophilic attack of hydroxide ion at the pyridinium ring. This reaction with pKa - 14.4 is unique among 1-methylpyridiniumcarboxaldehydes for the 3-isomer.