Carbanions from decarboxylation of orotate analogs: stability and mechanistic implications.
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.
Yeoh
Fong Ying
FY
Department of Chemistry and Biochemistry, San Francisco State University, San Francisco, CA 94132, USA.
Cuasito
Roxanne R
RR
Capule
Christina C
CC
Wong
Freeman M
FM
Wu
Weiming
W
D000838:Anions / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D003653:Decarboxylation; D009963:Orotic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D011728:Pyridones / Q000737:chemistry
D000838:Anions; D002264:Carboxylic Acids; D011728:Pyridones; D009963:Orotic Acid