Abstract
The geometry, energy, dipole moment and total atomic charge distribution have been calculated for torsional angles of 0°, 30°, 60° and 90° with respect to rotation about the CO bond in phenol using the 6-31G basis set, assuming that the ring, the bonded O-atom, and the ring H-atoms all lie in the same plane, but otherwise with full geometry optimization. Additional calculations, using the 6-31G* (5D) basis set, showed very similar changes in geometry in going from the 0° (planar) to the 90° structure. Complete relaxation of the planarity constraint results in the ring taking up a very shallow boat-type conformation, o<O 7C 1⋯C 4 = 1.4°, and a change in energy of only 0.05 kcal mol −1. Evidence for an attractive interaction between the oxygen lone pair and the nearest ring hydrogens is discussed.
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