Enthalpies of hydrogenation and formation of enones. Resonance energies of 2-cyclopentenone and 2-cyclohexenone

Donald W. Rogers, Yeping Zhao, Marit Traetteberg, Martin Hulce, Joel Liebman

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Abstract

The enthalpies of hydrogenation of 2-cyclopentenone, 2-cyclohexenone, 2-methyl-3-isobutoxycyclohex-2-enone, and 5-methylhex-5-en-2-one have been measured and found to be -(97.1 ± 2.7) kJ·mol-1, -(109.2 ± 2.9) kJ·mol-1, -(106.1 ± 3.0) kJ·mol-1, and -(113.2 ± 2.7) kJ·mol-1, respectively. In combination with the enthalpies of formation of the corresponding alkanones, we obtained the enthalpies of formation ΔfHo m (cyclopentenone) = -(100.3 ± 3.0) kJ·mol-1 and ΔfHo m (cyclohexenone) = -(121.9 ± 3.0) kJ·mol-1. By using isodesmic reactions, the resonance energy of cyclic enones is estimated to be (13 ± 4) kJ·mol-1.

Original languageEnglish
Pages (from-to)1393-1400
Number of pages8
JournalJournal of Chemical Thermodynamics
Volume30
Issue number11
StatePublished - Nov 1998

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Hydrogenation
hydrogenation
Enthalpy
enthalpy
energy
cyclopentenone
2-cyclohexen-1-one

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry

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Enthalpies of hydrogenation and formation of enones. Resonance energies of 2-cyclopentenone and 2-cyclohexenone. / Rogers, Donald W.; Zhao, Yeping; Traetteberg, Marit; Hulce, Martin; Liebman, Joel.

In: Journal of Chemical Thermodynamics, Vol. 30, No. 11, 11.1998, p. 1393-1400.

Research output: Contribution to journalArticle

Rogers, Donald W. ; Zhao, Yeping ; Traetteberg, Marit ; Hulce, Martin ; Liebman, Joel. / Enthalpies of hydrogenation and formation of enones. Resonance energies of 2-cyclopentenone and 2-cyclohexenone. In: Journal of Chemical Thermodynamics. 1998 ; Vol. 30, No. 11. pp. 1393-1400.
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N2 - The enthalpies of hydrogenation of 2-cyclopentenone, 2-cyclohexenone, 2-methyl-3-isobutoxycyclohex-2-enone, and 5-methylhex-5-en-2-one have been measured and found to be -(97.1 ± 2.7) kJ·mol-1, -(109.2 ± 2.9) kJ·mol-1, -(106.1 ± 3.0) kJ·mol-1, and -(113.2 ± 2.7) kJ·mol-1, respectively. In combination with the enthalpies of formation of the corresponding alkanones, we obtained the enthalpies of formation ΔfHo m (cyclopentenone) = -(100.3 ± 3.0) kJ·mol-1 and ΔfHo m (cyclohexenone) = -(121.9 ± 3.0) kJ·mol-1. By using isodesmic reactions, the resonance energy of cyclic enones is estimated to be (13 ± 4) kJ·mol-1.

AB - The enthalpies of hydrogenation of 2-cyclopentenone, 2-cyclohexenone, 2-methyl-3-isobutoxycyclohex-2-enone, and 5-methylhex-5-en-2-one have been measured and found to be -(97.1 ± 2.7) kJ·mol-1, -(109.2 ± 2.9) kJ·mol-1, -(106.1 ± 3.0) kJ·mol-1, and -(113.2 ± 2.7) kJ·mol-1, respectively. In combination with the enthalpies of formation of the corresponding alkanones, we obtained the enthalpies of formation ΔfHo m (cyclopentenone) = -(100.3 ± 3.0) kJ·mol-1 and ΔfHo m (cyclohexenone) = -(121.9 ± 3.0) kJ·mol-1. By using isodesmic reactions, the resonance energy of cyclic enones is estimated to be (13 ± 4) kJ·mol-1.

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