Interaction in trans-2-halocyclohexanols — an infrared and theoretical study

The O–H and C–O stretching frequencies of trans-2-halocyclohexanols in CCl₄ solutions have been measured and theoretical calculations have been performed to elucidate the main interactions, which are responsible for the conformational equilibria in these systems. It can be concluded that hydrogen bonding is predominant for trans-2-fluorocyclohexanol, leading to a stabilization of the eq–eq conformation, while for the chlorine, bromine and iodine derivatives, besides hydrogen bonding, gauche and steric interactions are also present.