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Logic Puzzle #11: Pairwise Correlation Confidence … Solution

Long range 2D NMR experiments do not necessarily provide information about all the connectivities. The following structure elucidation problem set is one such example.

Based on the 1H-13C HMBC shown below, there is no evident correlation between the 1H at 5.31 ppm and the 13C at 21.1 ppm. Note the green box describes the region of interest.

The correlation between the methyl 1H at 2.15 ppm and 13C at 84.7 ppm (indicated by the purple arrow and the red bonds below) is a weak 4J coupling (also denoted as a W-coupling or M-coupling). The coupling arises from the individual methyl protons rotating and interacting through a W-relationship (or M-)with the carbon. This coupling is not evident for the methine 1H at 5.31 ppm and the 13C at 21.1 ppm.

Thank you Serge for your comment.