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

doi:10.1006/jcht.1998.0407

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

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 Δ_fH^o _m (cyclopentenone) = -(100.3 ± 3.0) kJ·mol^-1 and Δ_fH^o _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 language	English (US)
Pages (from-to)	1393-1400
Number of pages	8
Journal	Journal of Chemical Thermodynamics
Volume	30
Issue number	11
DOIs	https://doi.org/10.1006/jcht.1998.0407
State	Published - Nov 1998

All Science Journal Classification (ASJC) codes

Atomic and Molecular Physics, and Optics
Materials Science(all)
Physical and Theoretical Chemistry

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@article{6f991d00b23341908fea7e465bbf9f17,

title = "Enthalpies of hydrogenation and formation of enones. Resonance energies of 2-cyclopentenone and 2-cyclohexenone",

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.",

author = "Rogers, {Donald W.} and Yeping Zhao and Marit Traetteberg and Martin Hulce and Joel Liebman",

year = "1998",

month = nov,

doi = "10.1006/jcht.1998.0407",

language = "English (US)",

volume = "30",

pages = "1393--1400",

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T1 - Enthalpies of hydrogenation and formation of enones. Resonance energies of 2-cyclopentenone and 2-cyclohexenone

AU - Rogers, Donald W.

AU - Zhao, Yeping

AU - Traetteberg, Marit

AU - Hulce, Martin

AU - Liebman, Joel

PY - 1998/11

Y1 - 1998/11

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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DO - 10.1006/jcht.1998.0407

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SN - 0021-9614

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

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