Infrared Study of β-Propiolactone in Various Solvent Systems and Other Lactones

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Many lactones exhibit two significant bands in the carbonyl stretching region which result from Fermi resonance interaction between νC=O and a combination or overtone of a lower-lying fundamental (or fundamentals). However, for β-propiolactone, three significant bands in the carbonyl stretching region of the spectrum are observed. These bands result from νC=O in Fermi resonance between the combination tone ν6 + ν13,A' and 2ν10,A'. The extent of Fermi resonance interaction between νC=O and the combination and/or overtone is dependent upon the solvent system. Approximate unperturbed νC=O frequencies have been calculated, and these νC=O frequencies decrease in frequency in the solvent order n-hexane, carbon tetrachloride, and chloroform. The unpertrbed νC=O frequencies were also calculated with the use of reported frequencies and band intensities for many other lactones, and the unpertubed νC=O frequencies decrease significantly as the amount of ring strain is reduced in the lactone structures. An equation, based on perturbation theory for obtaining approximate unperturbed νC=O frequencies for situations where three modes are in Fermi resonance, was developed and used to assign the unperturbed νC=O frequencies for β-propiolactone in various solvent systems. This method assumes that all or nearly all of the intensity in the three bands in Fermi resonance arises from the νC=O mode.

Keywords: Fermi resonance; Infrared; Molecular structure; Solvent effects

Document Type: Research Article


Affiliations: Analytical Sciences, 1897 Building, Dow Chemical Company, Midland, Michigan 48667

Publication date: June 1, 1991

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