6201-05-4Relevant academic research and scientific papers
Thermochemical Studies of Carbonyl Reactions. 4. Enthalpies of Hydrolysis of Norbornyl Ketals
Wiberg, Kenneth B.,Cunningham, Wells C.
, p. 679 - 684 (2007/10/02)
The dimethyl ketals of norbornanone and of eight methyl-substituted norbornanones were prepared, and the enthalpies of hydrolysis were determined.The compounds were chosen to provide a variety of steric interactions between the methyl substituents and the ketal group, much of which would be relieved on going to the ketone.The enthalpies of reaction varied by over 4 kcal/mol.The experimental data were modeled by molecular mechanics (MM2), and although a good correlation was found for the less substituted compounds, the ketal of camphor fell off the slope = 1 correlation line.The free energy changes were determined, and were found not to be well correlated with the enthalpy changes.
