The Conformational Equilibrium of 1,2,3-Tribromopropane in Solution

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Abstract
The p.m.r. spectra of dilute solutions of 1,2,3-tribromopropane in carbon tetrachloride, acetonitrile, and dimethylsulfoxide as well as of the neat compound are examined. From the three- and four-bond spin–spin coupling constants and from a comparison between observed and calculated dipole moments it is concluded that in nonpolar solvents the title compound exists preferably in the enantiomeric conformations a and i. In polar solvents other rotamers contribute to the equilibrium but still seem to play only a minor role. Semiempirical calculations of conformational energies rule out contributions to the conformational equilibrium from rotamers having (1:3) bromine–bromine interactions, but otherwise are only in moderate agreement with experiment.

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