A Computational Model for the Stereoelectronic Effects of Carboxylate Lone Pairs
by Kamitakahara, A.; Pranata, J.
The effects of carboxylate syn and anti lone pairs on the basicity of a water molecule were investigated using a combination of ab initio calculations and Monte Carlo simulations. This system serves as a quantitative computational model for the stereoelectronic effects of the carboxylate lone pairs. It was found that there is only a small difference in reactivity for this particular situation (1 kcal mol(-1)), in agreement with recent results and suggesting that earlier ideas overestimated the magnitude of the stereoelectronic effect.
- Journal
- Bioorganic Chemistry
- Volume
- 23
- Issue
- 3
- Year
- 1995
- Start Page
- 256-262
- URL
- https://dx.doi.org/10.1006/bioo.1995.1019
- ISBN/ISSN
- 1090-2120; 0045-2068
- DOI
- 10.1006/bioo.1995.1019