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Quantum mechanical origin of the stereoelectronic effects in the preferred conformation of compounds 2 and 6. (A) Overlap of σ (or n) and σ* orbitals that gives rise to the gauche effect. (B) Overlap of the lone pair and π* orbital that gives rise to the n→π* interaction; depictions were generated with NBOView 1.1 (Wendt and Weinhold 2001).
