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15444360037
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note
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This fact is also in agreement with theory. The geometry of menthol is such that it is hindered from one side, destabilizing the G-form in the adduct from the S enantiomer (see Table 1). This can be seen on the energy contour map (see Figure 5). The linear conformer is more stable, and the barrier to interconversion (G+G-) is higher. The menthol adduct prefers a linear structure.
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29
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15444342474
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note
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AB (R) although ΔE(R) < ΔE(S)]. According to calculations, these protons are affected by the shielding/deshielding effects of the aryl ring in a different manner in the respective conformers in R and S (see Figure 6). Figure 6 predicts small differences in the NMR behavior of 5.
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30
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