Carbanions from decarboxylation of orotate analogs: stability and mechanistic implications

Bioorg Chem. 2007 Aug;35(4):338-43. doi: 10.1016/j.bioorg.2007.02.001. Epub 2007 Apr 2.

Abstract

The pKa's of the 6-CH groups of 1,3-dimethyluracil, N-methyl-2-pyridone, and N-methyl-4-pyridone were determined through their reactions with bases derived from carbon acids with known pKa and the reactions of their corresponding carbanions with the carbon acids. No correlation between the stability of the carbanions and the rate of decarboxylation of corresponding carboxylic acids was found.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry*
  • Carboxylic Acids / chemistry
  • Decarboxylation
  • Orotic Acid / analogs & derivatives*
  • Orotic Acid / chemistry
  • Pyridones / chemistry

Substances

  • Anions
  • Carboxylic Acids
  • Pyridones
  • Orotic Acid