Applications of molecular mechanics calculations in carbohydrate chemistry. I. Conformational and constitutional equilibria of tetraoxabicyclo[4.4.0]- and -[5.3.0] decanes, bicyclic diacetals of alditols
✍ Scribed by Ulrich Burkert
- Publisher
- John Wiley and Sons
- Year
- 1980
- Tongue
- English
- Weight
- 539 KB
- Volume
- 1
- Category
- Article
- ISSN
- 0192-8651
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
The energies of various conformations have been calculated by molecular mechanics for cis and trans isomers of 2,4,7,9‐tetraoxabicyclo[4.4.0] decane and 3,5,8,10‐tetraoxabicyclo[5.3.0]decane and their methyl derivatives. These molecules are models for reaction products from formaldehyde and the tetrols, pentitols, and hexitols. The conformational equilibria were analyzed for the cis‐bicyclo [4.4.0] and cis‐bicyclo[5.3.0] systems and compared with available experimental data. The thermodynamic stability of bicyclo[4.4.0] products was found to be higher than that of bicyclo[5.3.0] derivatives in the gas phase in every case studied. Discrepancies with experimental data that exist in a few cases can be ascribed to solvent effects.