title: Thermochemical studies of epoxides and related compounds.
abstract: 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.
authors.affiliation: Department of Chemistry, Xavier University of Louisiana, 1 Drexel Drive, New Orleans Louisiana 70125, United States. kmmorgan@xula.edu
authors.forename: Kathleen M
authors.initials: KM
authors.lastname: Morgan
authors.forename: Jamie A
authors.initials: JA
authors.lastname: Ellis
authors.forename: Joseph
authors.initials: J
authors.lastname: Lee
authors.forename: Ashley
authors.initials: A
authors.lastname: Fulton
authors.forename: Shavonda L
authors.initials: SL
authors.lastname: Wilson
authors.forename: Patrick S
authors.initials: PS
authors.lastname: Dupart
authors.forename: Rosanna
authors.initials: R
authors.lastname: Dastoori
mesh_terms: D000475:Alkenes / Q000737:chemistry; D004735:Energy Transfer; D004852:Epoxy Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D044367:Phase Transition; D013440:Sulfides / Q000737:chemistry; D013816:Thermodynamics; D014835:Volatilization
chemical_list: D000475:Alkenes; D004852:Epoxy Compounds; D013440:Sulfides
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