Hydrolysis of α-chloro-substituted 2- and 4-pyridones: Rate enhancement by zwitterionic structure
2012
Tan, Ronald C. | Vien, Janie Q.T. | Wu, Weiming
The hydrolysis of α-chloro-N-methyl-4-pyridone was found to be more than five times faster than that of α-chloro-N-methyl-2-pyridone. Structural studies of 2- and 4-pyridones have revealed the higher polarity and greater extent of zwitterionic content in 4-pyridone. The results are thus consistent with the hypothesis that polarization and higher zwitterionic content in the heterocyclic structures enhances the rate of hydrolysis in α-substituted pyridone and uracil derivatives.
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