INFRARED MATRIX ISOLATION SPECTROSCOPIC STUDIES OF THE COMPLEXES OF CYCLOPROPANE AND METHYL-SUBSTITUTED CYCLOPROPANES WITH THE HYDROGEN HALIDES
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Date
1984
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Ohio State University
Abstract
Infrared matrix isolation spectroscopy has been used to isolate and characterize the 1:1 complexes formed by the hydrogen halides and cyanide with cyclopropane and avariety of methyl-substituted cyclopropanes. Perturbed modes of the cyclopropane ring were observed for each of the complexes studied, and a reduction in symmetry was noted for the cyclopropane complexes. In addition, the H-X stretching mode in the complex appeared shifted to lower energies, by up to $200 cm^{-1}$, indicating the formation of a hydrogen bond. The magnitude of the shift and the degree of perturbation of the ring correlated with the strength of interaction and dipole moment of the acid. The spectral results are in agreement with the structure of the $HX \cdot c-C_{3}H_{6}$ complexes as determined by rotational spectroscopy in supersonic jets. The site of coordination in the methyl-substituted cyclopropane is not known, and these studies may shed additional light on the mechanism of acid-catalyzed ring openings of substituted cyclopropanes.
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Author Institution: Department of Chemistry, University of Cincinnati