An axialtert-butyl group in strained cyclohexene: X-ray analysis and theoretical calculations of 2-(2-tert-butylcyclohex-3-enyl)propan-2-ol

Abstract

The structure of the title compound, C(13)H(24)O, (I), shows a sofa conformation of the ring with two pseudo-axial substituents. The dihedral angle between these substituents is 131.56 (12) degrees . Calculations using the B3LYP/6-31G* level of theory show two minima, one corresponding to the crystal structure and the other to a boat conformation of the ring with two equatorial substituents. The energy of this latter conformation is 17.4 kcal mol(-1) higher than that of (I). The molecule forms an infinite co-operative hydrogen-bonded chain running in the b direction.