6533b861fe1ef96bd12c42e6
RESEARCH PRODUCT
Theoretical Study of the Gas Phase Decomposition of Glycolic, Lactic, and 2-Hydroxyisobutyric Acids
Vicent S. SafontVicent MolinerJuan AndrésLuis R. Domingosubject
Reaction mechanismChemistryChemical process of decompositionAb initioGeneral ChemistryBiochemistryDecompositionCatalysischemistry.chemical_compoundColloid and Surface ChemistryNucleophileGroup (periodic table)Computational chemistryPotential energy surfaceOrganic chemistryCarbon monoxidedescription
The reaction mechanism associated with the decomposition of three α-hydroxycarboxylic acids (glycolic, lactic, and 2-hydroxyisobutyric) in the gas phase to form carbon monoxide, water, and the corresponding carbonyl compounds has been theoretically characterized by using ab initio analytical gradients at the MP2 level of theory with the 6-31G** and 6-31++G** basis sets. A detailed characterization of the potential energy surface points out the existence of three competitive reaction pathways for the decomposition process. The first pathway describes a two-step mechanism, with water elimination and formation of an α-lactone intermediate, achieved by the nucleophilic attack of the carbonylic oxygen atom of the carboxyl group (mechanism A). The second pathway is also a two-step mechanism, but in this case the formation of the α-lactone is obtained by means of the nucleophilic attack of the hydroxylic oxygen atom of the carboxyl group (mechanism B). These two pathways share a common second step in which the α...
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1997-07-01 | Journal of the American Chemical Society |