Journal of Physical Chemistry p. 2025 - 2030 (1984)
Update date:2022-08-16
Topics:
Hillig, Kurt W.
Kuczkowski, Robert L.
Cremer, Dieter
The microwave spectra of five isotopic species of cis-difluoroethylene ozonide (cis-3,5-difluoro-1,2,4-trioxolane) were assigned, including the parent, both the d1 and the d2 species, and the symmetric double-18O and the triple-18O species.A series of vibrational satellites also accompanied the ground-state transitions.The average structure consistent with this data was an ether oxygen envelope conformation having Cs symmetry, with the fluorines axial to the ring.Ab inito calculations were performed for selected values of the pseudorotational phase angle Φ to provide additional insights.They indicated that the ether envelope corresponded to the minimum-energy conformer.The potential function vs. Φ was relatively flat near the minimum and did not possess a low-energy path corresponding to the usual pseudorotation motion.Instead, the energy valley connecting puckered forms at 180, 90, and 270 deg terminates at the planar form.The ground-state conformation was discussed in terms of the balance between ring-substituent, substituent-substituent, and puckering fores.Stabilizing ring-substituent interactions dominate this interplay and are also reflected in long C-F and short C-O bond distances indicative of anomeric interactions involving the fluorine substituents.
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