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 perfor med to elucidate the main interactions, which are responsible for the confo rmational equilibria in these systems. It can be concluded that hydrogen bo nding is predominant for trans-2-fluorocyclohexanol, leading to a stabiliza tion of the eq-eq conformation, while for the chlorine, bromine and iodine derivatives, besides hydrogen bonding, gauche and steric interactions are a lso present. (C) 2001 Elsevier Science B.V. All rights reserved.