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Thermochemical Studies of Epoxides and Related Compounds

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Department of Chemistry, Xavier University of Louisiana, 1 Drexel Drive, New Orleans Louisiana 70125, United States
Cite this: J. Org. Chem. 2013, 78, 9, 4303–4311
Publication Date (Web):April 3, 2013
https://doi.org/10.1021/jo4002867
Copyright © 2013 American Chemical Society
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Abstract

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Gas-phase heats of formation for the four butene oxide isomers are reported. They were obtained by measuring the condensed-phase heat of reduction to the corresponding alcohol using reaction calorimetry. Heats of vaporization were determined and allow gas-phase heats of formation to be obtained. The experimental measurements are compared to calculations obtained using a variety of computational methods. Overall, the G3 and CBS-APNO methods agree quite well with the experimental data. The influence of alkyl substituents on epoxide stability is discussed. Comparisons to alkenes, cyclopropanes, aziridines, thiiranes, and phosphiranes are also made. Isodesmic-type reactions were used to determine strain energies of the epoxides and related compounds with various substituents.

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Reaction calorimetry data; vapor pressure–temperature data from ebuillometry; heat capacities used in corrections to heats of vaporizations; tabulation of calculated energies and thermal energy corrections, or enthalpies; optimized geometries from G3 calculations. This material is available free of charge via the Internet at http://pubs.acs.org.

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