When anomeric effects collide

Christopher J. Cramer, Anne Marie Kelterer, Alfred D. French

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Rotational coordinates about the C(3)-O(4) bonds of 2,4-dioxaheptane (DOH) and 2,4,6-trioxaheptane (TOH) are compared at correlated levels of electronic structure theory for gauche and trans orientations of the O(2)-C(3) bonds. TOH has overlapping anomeric effects, while DOH does not. The overlapping stereoelectronic effect shows its largest impact on the length of the O(2)-C(3) bond, which is typically 0.02 Å longer in DOH than in TOH. However, the energetic consequences of the overlapping anomeric effect in TOH are very small, as judged by total conformational energies and analysis of delocalization energies within a natural bond orbital framework.

Original languageEnglish (US)
Pages (from-to)1194-1204
Number of pages11
JournalJournal of Computational Chemistry
Volume22
Issue number11
DOIs
StatePublished - Aug 2001

Keywords

  • Anomeric effects
  • Hyperconjugation
  • Polyethers
  • Rotational coordinates

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