ESR characterization of ring-closed oxirane radical cations via a novel alternating line width effect

Journal Article · Tue Nov 24 23:00:00 EST 1987 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00258a045· OSTI ID:5527997

Williams, F; Dai, S; Snow, L D; Qin, X Z; Bally, T; Nitsche, S; Haselbach, E; Nelsen, S F; Teasley, M F

There is considerable experimental evidence supported by numerous theoretical studies to show that the radical cation formed from oxirane under both gas-phase and solid-state conditions is the planar C...C ring-opened oxallyl isomer. In fact, the low barrier to the isomerization usually dictates that only the ring-opened form can be detected spectroscopically from monocyclic and bicyclic oxiranes at 77 K. These elusive cyclic cations should be accessible, however, in polycyclic oxiranes where steric constraints prevent C...C opening of the oxirane ring, and here the authors report the first ESR characterization of ring-closed oxirane cations with a one-electron C-C bond.

• Research Organization: Univ. of Tennessee, Knoxville
• OSTI ID: 5527997
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 109:24; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
CATIONS
CHARGED PARTICLES
DATA
ELECTRON SPIN RESONANCE
EPOXIDES
EXPERIMENTAL DATA
INFORMATION
IONS
LOW TEMPERATURE
MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
RADICALS
RESONANCE
STRUCTURAL CHEMICAL ANALYSIS
TEMPERATURE DEPENDENCE