ArticleThe Journal of organic chemistry2022
Hyperconjugative Interactions of the Carbon-Halogen Bond that Influence the Geometry of Cyclic α-Haloacetals.
Article in The Journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Influence of Halogen Atoms and the Reactivity of Nucleophiles on Reactions of Tetrahydropyran and Tetrahydrofuran Acetals withThe Journal of organic chemistry · 2025Article
- Stereoselective synthesis of geminal bromofluoroalkenes by kinetically controlled selective conversion of oxaphosphetane intermediates.Science advances · 2024Article
- Neighboring-Group Participation by C-2 Acyloxy Groups: Influence of the Nucleophile and Acyl Group on the Stereochemical Outcome of Acetal Substitution Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Feedback Inhibition of Bacterial Nucleotidyltransferases by Rare Nucleotide l-Sugars Restricts Substrate Promiscuity.Journal of the American Chemical Society · 2023Article
- Characterization and Fate of a Septanosyl Ferrier Cation in the Gas and Solution Phases.The Journal of organic chemistry · 2023Article
- Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
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Authors and funding
3 authors.
Funding
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.
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Registered trials
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