V. Kalasinsky, C. Wurrey
Oct 1, 1980
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Influential Citations
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Journal
Journal of Raman Spectroscopy
Abstract
The IR and Raman spectra (4000–50 cm−1) of (chloromethyl)cyclopropane and epichlorohydrin have been recorded in all three physical states. It has been concluded from the spectroscopic data and from variable temperature studies that (chloromethyl)cyclopropane exists as an equilibrium mixture of gauche (95%) and cis (5%) conformers in the liquid state, while only the gauche form persists in the solid phase. The enthalpy difference between these two rotamers was found to be 1.40±0.10 kcal mol−1. Similarly, epichlorohydrin has also been shown to exist as an equilibrium mixture of gauche-1 (70%), gauche-2 (21%) and cis (9%) conformers in the liquid state, with only the gauche-1 form remaining in the solid phase. Enthalpy differences among these conformers were determined to be 1.2±0.2 kcal mol−1 (gauche-1 vs. cis) and 0.70±0.10 kcal mol−1 (gauche-1 vs gauche-2). Apparently steric repulsions between the chlorine atom and β ring-hydrogens destabilize the cis conformation in each molecule. For each molecule, a vibrational assignment has also been proposed.