Stability trends in carbocation intermediates stemming from germacrene A and hedycaryol

Naziha Tarannam, Prashant Kumar Gupta, Shani Zev, Dan Thomas Major

Research output: Contribution to journalArticlepeer-review

Abstract

In the current work, we analyzed the origin of difference in stabilities among the germacrene A and hedycaryol-derived carbocations. This study focused on twelve hydrocarbons derived from germacrene A and twelve from hedycaryol, which can be divided into three groups: four molecules containing 6-6 bicyclic rings, four 5-7 bicyclic compounds with the carbocation being on the seven-membered ring and the remaining four 5-7 bicyclic compounds with the carbocation on the five-membered ring. The variations in energy within the groups of carbocations (i.e., 6-6 and two kinds of 5-7 bicyclic carbocations) can be ascribed to intramolecular repulsion interactions, as seen from non-covalent interactions plots. Despite the structural similarities between germacrene A and hedycaryol cations, they possess a somewhat different stability trend. These differences are attributed to C+···OH intramolecular interactions present in some hedycaryol cations, which are absent in the carbocations derived from germecrene A.

Original languageEnglish
Pages (from-to)1189-1197
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume20
DOIs
StatePublished - 2024

Bibliographical note

Publisher Copyright:
© 2024 Tarannam et al.;

Keywords

  • carbocation
  • germacrene A
  • hedycaryol
  • stability trend
  • terpenes

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