Abstract

Abstract The M06–2X, B3LYP, ωB97XD and B97D functionals with the 6–311++G(2d,2p) and DGDZVP basis sets were used to describe the stationary points of minimum energy of the potential energy surface of perezone. The inability of theoretical methods to predict a consistent conformational order, including the effects of zero point energy and dielectric constant was highlighted. Perezone was used as a model of study since it is known that weak interactions are involved in its conformation and represent a challenge of study for theoretical methods. Each level of theory here employed generated a significantly different conformational population, ranging from 75% participation of folded conformers (where a π/π stabilizing interaction was predicted) to less than 5%, without producing a uniform conformational order. Surprisingly, in every case, the constructed Vibrational Circular Dichroism (VCD) spectrum with each level of theory was able to reproduce the experimental spectrum with high level of confidence. The correct R configuration of the stereogenic center of perezone was predicted in all cases.

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