INDO- and CNDO-Approximated Molecular Orbital Calculations on the Spin-Spin Coupling Constants in Some 2-Substituted Oxetanes

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Abstract
Spin-spin coupling constants between the methine proton in the oxetane ring and the phenyl protons and carbon nuclei have been calculated in different conformations in the INDO approximation for 2-phenyloxetane and 2-(4-fluorophenyl) oxetane, and in the CNDO approximation for 2-(2- chlorophenyl) oxetane and 2-(3-chlorophenyl) oxetane. In each case the finite perturbation method has been used. In the case of 2-(2-chlorophenyl) oxetane a fairly high energy barrier for the rotation around the C-C bond between the rings is obtained, while in the other three cases the barrier is much lower. The calculations predict an equilibrium conformation in which the oxygen atom lies almost in the plane of the aromatic ring. The calculated dipole moments of 2-(2-chlorophenyl) oxetane and 2-(3-chlorophenyl) oxetane vary significantly with conformation.

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