Hyperconjugative Interactions of the Carbon-Halogen Bond that Influence the Geometry of Cyclic α-Haloacetals

Krystyna M. Demkiw, Chunhua T. Hu, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

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 languageEnglish (US)
Pages (from-to)5315-5327
Number of pages13
JournalJournal of Organic Chemistry
Volume87
Issue number8
DOIs
StatePublished - Apr 15 2022

ASJC Scopus subject areas

  • Organic Chemistry

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