70160-88-2Relevant academic research and scientific papers
Hydrolysis and carbonyl-oxygen exchange in tertiary amides. Estimation of the free energy changes for breakdown and conformational changes of tetrahedral intermediates
Deslongchamps, Pierre,Barlet, Roger,Taillefer, Roland J.
, p. 2167 - 2172 (2007/10/02)
Second order rate constants were measured at several temperatures for the basic hydrolysis and for concurrent carbonyl-oxygen exchange with solvent for N-benzyl-N-methylformamide-18O.N-benzyl-N-methyltrideuteroacetamide-18O, and N-benzyl-N-methyl-α,α-dideuteropropionamide-18O.Carbonyl-oxygen exchange with solvent is rationalized by invoking a conformational change in the tetrahedral intermediate.Energy barriers for these conformational changes are estimated to be of the order of 5.6, 8.0, 8.2 kcal/mol respectively for the above amides.
