Monodeuterated methyl groups have previously been demonstrated to provide access to long-lived nuclear spin states. This is possible when the CH2 D rotamers have sufficiently different populations and the local environment is chiral, which foments a non-negligible isotropic chemical shift difference between the two CH2 D protons. In this article, the focus is on the N-CH2 D group of N-CH2 D-2-methylpiperidine and other suitable CH2 D piperidine derivatives. We used a combined experimental and computational approach to investigate how rotameric symmetry breaking leads to a 1H CH2 D chemical shift difference that can subsequently be tuned by a variety of factors such as temperature, acidity and 2-substituted molecular groups.
Elliott, S.J.; Ogba, O.M.; Brown, L.J.; O’Leary, D.J. An Examination of Factors Influencing Small Proton Chemical Shift Differences in Nitrogen-Substituted Monodeuterated Methyl Groups. Symmetry 2021, 13, 1610. https://doi.org/10.3390/sym13091610
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