If one is told that a sterically less hindered group is equally likely to accept hydrogen bonding than a more hindered group, it initially feels contradictory with common organic chemistry concepts. In this study, we investigate such a case, in which the intuitive assumption that a hydrogen-bond-accepting solvent like DMSO would preferably bind to the sterically less hindered side, does not hold. Using vibrational circular dichroism (VCD) spectroscopy, the bindong of DMSO to the chiral 2,6-pyridinediyl-dialkylamide derivates is indee shown to occur with equal likelihoods for two sterically differently schielded amide protons.
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