Conformational preferences of chiral molecules: free jet rotational spectrum of 1-phenyl-1-propanol

Abstract

The rotational spectra of normal and O-d species of the two most stable conformers of chiral 1-phenyl-1-propanol, obtained by free jet millimetre-wave absorption spectroscopy reveal that both conformers are stabilized by a O–H⋯π interaction, and have the Cα–Cβ-bond oriented nearly perpendicular to the plane of the benzene ring. The methyl group is trans with respect to the phenyl group for the most stable conformer (T), while it is gauche with respect to the phenyl group and entgegen with respect to the hydroxyl group for the second most stable conformer (GE). The energy difference (E_GE − E_T) was estimated to be 50(50) cm⁻¹ from relative intensity measurements.