n,π-Interactions in Polycyclic Unsaturated Ketones: Photoelectron Spectroscopic Study

Branka Kovač, Igor Novak, Kata Mlinarić-Majerski, Marijana Vinković, Mira Kaselj

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1 Citation (Scopus)


He I photoelectron spectra (PE) of several β,γ-unsaturated polycyclic ketones, their parent ketones, and alkenes have been measured. The assignment of spectra is based on semiempirical MO calculations (PM3 method) and empirical arguments. Endo-derivatives showed larger HOMO/SHOMO band separation than exo-cyclic unsaturated ketones. The results of MO calculations are in good agreement with this general trend. Strikingly different photochemical transformations and π* ⟸ n electronic transition intensities, exhibited by the two groups of compounds, can be rationalized within the framework of oxygen lone pair ↔ π bond interactions.

Original languageEnglish
Pages (from-to)3033-3036
Number of pages4
JournalJournal of Organic Chemistry
Issue number11
Publication statusPublished - 01 Jun 1994


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