On the Stable Relative Orientation of Groups Connected by a Carbon-Carbon Single Bond

Langseth and his co-workers [1] have recently applied the results of essentially incomplete spectroscopic studies of liquid cyclohexane, symmetrical tetrachloroethane, and ethylene deuterobromide to a discussion of the intramolecular forces restricting internal rotation about the C-C bond. We believe that none of their structural conclusions is correct. Their discussion is based on their conclusion that in these molecules the opposed or eclipse configurations are the stable ones. Insofar as liquid cyclohexane and symmetrical tetrachloroethane are concerned this conclusion is most probably incorrect since it directly contradicts the results of a great number of more straightforward studies of these and similar molecules.