An examination of factors influencing small proton chemical shift differences in nitrogen-substituted monodeuterated methyl groups
An examination of factors influencing small proton chemical shift differences in nitrogen-substituted monodeuterated methyl groups
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 a1 H CH2 D chemical shift difference that can subsequently be tuned by a variety of factors such as temperature, acidity and 2-substituted molecular groups.
CH D, Chemical shift difference, Diastereotopicity, Equilibrium isotope effects, Monodeuterated methyl group
Elliott, Stuart J.
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Ogba, O. Maduka
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Brown, Lynda J.
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O’leary, Daniel J.
46a2d9e6-69c3-4f41-a29d-155af09b4dc8
2 September 2021
Elliott, Stuart J.
6cc724de-f75f-4c0f-a00a-e712b4e73b12
Ogba, O. Maduka
b773ecc1-0ba8-4f75-84cc-fae34e382112
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
O’leary, Daniel J.
46a2d9e6-69c3-4f41-a29d-155af09b4dc8
Elliott, Stuart J., Ogba, O. Maduka, Brown, Lynda J. and O’leary, Daniel J.
(2021)
An examination of factors influencing small proton chemical shift differences in nitrogen-substituted monodeuterated methyl groups.
Symmetry, 13 (9), [1610].
(doi:10.3390/sym13091610).
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 a1 H CH2 D chemical shift difference that can subsequently be tuned by a variety of factors such as temperature, acidity and 2-substituted molecular groups.
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symmetry-13-01610-v2
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Accepted/In Press date: 26 August 2021
Published date: 2 September 2021
Keywords:
CH D, Chemical shift difference, Diastereotopicity, Equilibrium isotope effects, Monodeuterated methyl group
Identifiers
Local EPrints ID: 453554
URI: http://eprints.soton.ac.uk/id/eprint/453554
ISSN: 2073-8994
PURE UUID: cd39811a-a313-4a02-b2a6-85c78db518b4
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Date deposited: 19 Jan 2022 17:46
Last modified: 06 Jun 2024 01:37
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Contributors
Author:
Stuart J. Elliott
Author:
O. Maduka Ogba
Author:
Daniel J. O’leary
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