Understanding the thermal [1s,5s] hydrogen shift isomerization of ocimene

Eduardo Chamorro, Pablo Ruiz, Jairo Quijano, Diana Luna, Laura Restrepo, Sandra Zuluaga, Mario Duque-Noreña

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


α-Ocimene, β-ocimenes and alloocimenes are isomeric monoterpenes occurring naturally as oils within several plants and fruits. These thermally unstable compounds are employed in the pharmaceutical and fine-chemicals industries due to their natural plant defense properties and pleasant odors. In this work, and in the context of a recent revival in attention on the subject, we provide new theoretical insights concerning the nature of the electronic reorganization driving the decomposition of cis-β-ocimene to alloocimene. Our findings support the experimental proposal of a rearrangement via a six-membered cyclic transition state in a one-step concerted and highly synchronic process.

Original languageEnglish
Article number2390
JournalJournal of Molecular Modeling
Issue number8
Publication statusPublished - Aug 2014


  • DFT
  • ELF
  • Ocimene thermal decomposition
  • Six-membered transition state
  • [1s,5s] hydrogen shift

ASJC Scopus subject areas

  • Catalysis
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Computational Theory and Mathematics
  • Inorganic Chemistry


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