Protonated carbonic acid and reactive intermediates in the acidic decarboxylation of indolecarboxylic acids.
Elucidation of the mechanism for decarboxylation of indolecarboxylic acids over a wide range of solution acidity reveals the importance of protonated carbonic acid (PCA) as a reaction intermediate. In concentrated acid, the initial addition of water to the carboxyl group of the indolecarboxylic acid leads to a hydrated species that is capable of releasing PCA upon rate-determining carbon-carbon bond cleavage. The overall process is catalytic in water and acid, implicating PCA as a potential carboxylating reagent in the microscopic reverse reaction.
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S3H6.
Adelle A
AA
Vandersteen
Scott O C
SO
Mundle
Ronald
R
Kluger
D002255:Carbonic Acid / Q000737:chemistry*; D002264:Carboxylic Acids; D003653:Decarboxylation; D006863:Hydrogen-Ion Concentration; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011522:Protons
D002264:Carboxylic Acids; D007211:Indoles; D011522:Protons; C058980:indole-2-carboxylic acid; D002255:Carbonic Acid; C012382:indole-3-carboxylic acid