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The directional changes in torsion angles alone after complexation of the carbonyl oxygen with a prototypical cation such as H+ predict the facial selectivity of substituted cyclohexanones. An ab initio investigation

✍ Scribed by Duraiswamy A. Jeyaraj; Arpita Yadav; Veejendra K. Yadav

Book ID
104257269
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
258 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

H + was taken as a prototypical cation for complexation with the carbonyl oxygen of 3-oxa-, 3,5-dioxa-, and 3-thiacyclohexanones. The geometries of the complexes were fully optimized using ab initio MO calculations with 6-31G basis set. The complexation desymmetrizes the molecular geometry further to an extent that the torsion angle changes on the axial face can be rationally used for the prediction of the facial selectivity in reactions with nucleophiles. The torsion angle changes are sensitive to the nature, position, and orientation of the substituents.

πŸ“œ SIMILAR VOLUMES

3-Halocyclohexanones. Torsion angle chan
3-Halocyclohexanones. Torsion angle changes after cation-carbonyl complexation dictate the facial selectivity in reactions with nucleophiles: An ab initio investigation
✍ Duraiswamy A. Jeyaraj; Veejendra K. Yadav πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 254 KB

The geometrical changes that take place after complexation of the carbonyl oxygen of 3halocyclohexanones with prototypical cations such as H + and Li + were calculated using ab initio MO methods at 6-31G level. The torsion angle changes interpret rationally the experimentally known axial preference