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Interpretation of the Vibrational Spectra of Small Ring Systems: Matrix Isolation and Condensed Phase Studies of Perfluorocyclobutanone

Volume 31, Number 2 (April 1977) Page 164-166

Harris, W.C.; MacNamee, R.W.; Van Venrooy, J.R.

Although the equilibrium structure of four-membered ring systems can be understood in terms of a balance between the ring-strain and torsional forces, the resulting conformation of fluorinated derivatives of cyclobutane is more difficult to quantify. For example, the introduction of a CF2 group in cyclobutane reduces the barrier to planarity from 503 cm−1 (c-C4H8) to 241 cm−1 (c-C4H6F2). Since a similar reduction in barrier heights has also been reported for trimethylene oxide and 3,3-difluoroxetane, efforts have been initiated to understand these changes by considering variations in the torsional forces for fluorine-containing cyclic and open chain molecules. To complement our work in this area, the present vibrational study of Perfluorocyclobutanone (c-C4F6O) was undertaken in order to determine the skeletal structure of this molecule.