Abstract
A fundamental new type of non-opportunistic hydrogen bond was detected between a proximal C−H group and the selenium atom of a selenocarbonyl group in aldols of chiral N-acyl selones (see structure) by gradient-selected 1H–77Se HMQC NMR spectroscopy and X-ray crystallography. The C−H⋅⋅⋅Se=C interaction provides a possible explanation for the ability of chiral selone groups to interrogate remotely disposed chiral centers by 77Se NMR spectroscopy.
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