74173-58-3Relevant articles and documents
Synthesis, tautomeric forms, specific intermolecular interactions, and lipophilicity of methylated 6-hydroxypyridazine-3-carboxylic acid and its 4,5-dihydro analogs
Katrusiak, Anna,Piechowiak, Pawe?,Katrusiak, Andrzej
, p. 84 - 90 (2011)
Effects of methylation for intermolecular interactions and lipophilicity have been studied for a series of methylated 4,5-dihydro-6-hydroxypyridazine-3- carboxylic and 6-hydroxypyridazine-3-carboxylic acids (1 and 2). In solution they exist in equilibrium of the lactam and lactim tautomers, with the reverse preferences for analogs 1 and 2, which affect the syntheses of their methylated derivatives. Carboxylic acid 2 preferably crystallizes as a hydrate, built of carboxylate anions and hydronium cations 2-·H 3O+, hydrogen bonded into catemeric patterns involving both ions. In methyl 4,5-dihydro-6-oxopyridazine-3-carboxylate (4A) the molecules are NH?O hydrogen bonded into chains. In both structures 2 -·H3O+ and 4A, there are relatively strong CH?O hydrogen bonds, arranging the molecules into sheets. The increased lipophilicity of the methylated derivatives has been correlated with the formation of CH?O bonds.