The impacts of the generalized anomeric effect (GAE) and gauche effect (GE) associated with donor-acceptor electron delocalizations and dipole-dipole interactions on the conformationalbased methods and natural bond orbital (NBO) interpretation. Both methods used showed that the above compounds exist predominantly in the axial chair conformation and the axial conformation stability increased from 2-methoxy-(1) to 2-methylselenocyclohexanone oxime (3) and also from 2-fluoro-(4) to 2-bromocyclohexanone oxime (6). The NBO analysis showed that the GAE increases from compound 1 to compound 3 and also from compound 4 to compound 6. GE does not have significant impact on the conformational behaviors of compounds 1-6 and GAE succeeds in accounting qualitatively for the increase of the axial preferences in both series of compounds.