Stability trends in carbocation intermediates stemming from germacrene A and hedycaryol.

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

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Article in Beilstein journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1citing papers in PubMed

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1 citing paper in PubMed.

Direct Electrochemical Detection of Geosmin Using ZnACS omega · 2026
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4 authors.

Naziha Tarannam *Department of Chemistry and Institute of Nanotechnology and Advanced Materials, Bar-Ilan University, Ramat-Gan 52900, Israel.ORCID https://orcid.org/0000-0003-4656-5552

Prashant Kumar Gupta *Department of Chemistry and Institute of Nanotechnology and Advanced Materials, Bar-Ilan University, Ramat-Gan 52900, Israel.ORCID https://orcid.org/0000-0002-4792-7538

Shani ZevDepartment of Chemistry and Institute of Nanotechnology and Advanced Materials, Bar-Ilan University, Ramat-Gan 52900, Israel.

Dan Thomas MajorDepartment of Chemistry and Institute of Nanotechnology and Advanced Materials, Bar-Ilan University, Ramat-Gan 52900, Israel.ORCID https://orcid.org/0000-0002-9231-0676

Funding

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6 · The paper itself

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

Indexed as

carbocationgermacrene Ahedycaryolstability trendterpenes

Identifiers

PMID38887567

DOI10.3762/bjoc.20.101

PMCPMC11181226

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