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A curious case of dynamic disorder in pyrrolidine rings elucidated by NMR crystallography
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Szell, Patrick M. J., Brown, Steven P., Hughes, Leslie Peter, Blade, Helen and Nilsson Lill, Sten O. (2020) A curious case of dynamic disorder in pyrrolidine rings elucidated by NMR crystallography. Chemical Communications, 56 (90). pp. 14039-14042. doi:10.1039/D0CC05236A ISSN 1359-7345.
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WRAP-curious-case-dynamic-disorder-pyrrolidine-rings-lucidated-NMR-crystallography-Brown-2020.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution. Download (1332Kb) | Preview |
Official URL: https://doi.org/10.1039/D0CC05236A
Abstract
A pharmaceutical exhibits differing dynamics in crystallographically distinct pyrrolidine rings despite being nearly related by symmetry, with one performing ring inversions while the other is constrained to torsional librations. Using 13C solid-state magic-angle spinning (MAS) NMR and DFT calculations, we show that this contrast originates from C-H···H-C close contacts and less efficient C-H···π intermolecular interactions observed in the transition state of the constrained pyrrolidine ring, highlighting the influence of the crystallographic environment on the molecular motion.
Item Type: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry R Medicine > RS Pharmacy and materia medica |
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Physics | |||||||||
Library of Congress Subject Headings (LCSH): | Pharmaceutical chemistry, Crystallography, Pyrrolidine | |||||||||
Journal or Publication Title: | Chemical Communications | |||||||||
Publisher: | Royal Society of Chemistry | |||||||||
ISSN: | 1359-7345 | |||||||||
Official Date: | 21 November 2020 | |||||||||
Dates: |
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Volume: | 56 | |||||||||
Number: | 90 | |||||||||
Page Range: | pp. 14039-14042 | |||||||||
DOI: | 10.1039/D0CC05236A | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Access rights to Published version: | Open Access (Creative Commons) | |||||||||
Date of first compliant deposit: | 20 October 2020 | |||||||||
Date of first compliant Open Access: | 21 October 2020 | |||||||||
RIOXX Funder/Project Grant: |
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