An Examination of Factors Influencing Small Proton Chemical Shift Differences in Nitrogen-Substituted Monodeuterated Methyl Groups

Authors

Stuart J. Elliott, University of Liverpool
O. Maduka Ogba, Chapman UniversityFollow
Lynda J. Brown, University of Southampton
Daniel J. O'Leary, Pomona College

Document Type

Article

Publication Date

9-2-2021

Abstract

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.

Comments

This article was originally published in Symmetry, volume 13, in 2021. https://doi.org/10.3390/sym13091610

Recommended Citation

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

Copyright

The authors

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 License.