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Issue 12, 1986

Theoretical study of the mechanism of thermal decarboxylation of salicylic and p-aminobenzoic acids; models for aqueous solution

Abstract

The mechanism of decarboxylation of salicylic and p-aminobenzoic acids in aqueous solution has been investigated by ab initio methods using the STO-3G basis set and fully optimized geometries. Single-point 3–21G energy calculations were then performed to improve the results. The mechanism suggested is a pseudo-unimolecular concerted decomposition of the free acid by interaction with a chain of water molecules, the α-protonated form of the carboxylate anion representing the activated complex. In comparison with unsubstituted benzoic acid, the presence of ortho- and para-electron-releasing groups increases the electron density at the carbon atom next to the carboxy group, hence facilitating the approach of the electrophilic proton, and decreasing the activation energy.

Article information


J. Chem. Soc., Perkin Trans. 2, 1986, 1953-1959
Article type
Paper

Theoretical study of the mechanism of thermal decarboxylation of salicylic and p-aminobenzoic acids; models for aqueous solution

P. Ruelle, J. Chem. Soc., Perkin Trans. 2, 1986, 1953 DOI: 10.1039/P29860001953

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