Abstract
Abstract The conformational preference for gauche structures over anti ones in the simple model molecules CH4−nClnS (where n=1 and 2) was examined in detail by means of Natural Bond Orbital (NBO) analysis. We also compared the origin of the anomeric effect in CH2ClSH and CH2FSH. The energetic preference at MP2/6-311+G(d,p) level was slightly greater in CH2ClSH than in CHCl2SH. NBO analysis at the HF/6-311+G(d,p)//MP2/6-311+G(d,p) level indicates that the conformational preference for gauche conformers over anti ones is the result of a wide variety of orbital interactions. However, the interaction between the lp(S) and σ∗(C–Cl) is the most important factor for stabilizing the gauche conformers. In all compounds studied here, the effect of electrostatic and steric contributions involved in the Lewis term on stability of gauche conformers was less important than the charge delocalization.
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