title: Hydrolysis of α-chloro-substituted 2- and 4-pyridones: rate enhancement by zwitterionic structure.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, San Francisco State University, San Francisco, CA 94132, USA.
authors.forename: Ronald C
authors.initials: RC
authors.lastname: Tan
authors.forename: Janie Q T
authors.initials: JQ
authors.lastname: Vien
authors.forename: Weiming
authors.initials: W
authors.lastname: Wu
mesh_terms: D006868:Hydrolysis; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D011728:Pyridones; D014498:Uracil