Abstract
The analysis of the structures of low-energy conformers of different α-haloacetals reveals changes in bond lengths and geometries that correspond to stabilizing orbital interactions that contribute to the ground-state structures of these systems. Several factors, including the electron-donating and electron-accepting abilities of the substituents on the ring, affect the degree of the electronic interactions in these carbohydrate-like systems. The presence of an α-halogen atom that can participate in hyperconjugation has been shown to contribute to the structural characteristics of the low-energy conformer. The experimental evidence is supported by natural bond order (NBO) analysis to identify the types of interactions and to assess their relative importance.
Original language | English (US) |
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Pages (from-to) | 5315-5327 |
Number of pages | 13 |
Journal | Journal of Organic Chemistry |
Volume | 87 |
Issue number | 8 |
DOIs | |
State | Published - Apr 15 2022 |
ASJC Scopus subject areas
- Organic Chemistry