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The photoelectron spectra of a series of 1,3-cyclohexanediones and 1,3-cycIopentanediones and of acetylacetone and 3-ethoxy-2-cyclohexenone are reported. The inductive effect of a carbonyl group is estimated. Photoelectron spectra of some of the corresponding trans-tnolone tautomers, as well as that of the hydrogen-bonded cw-enolone of acetylacetone, are also reported, and assignments of the structures of the predominant tautomers in the gas phase and observations about the influence of substituents on gas phase tautomeric equilibria are made. Orbital assignments corresponding to each ionization are made by comparison of experimental ionization potentials with semiempirical calculations and by measuring alkyl substituent effects on the ionization potentials of the valence orbitals.

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