Issue 90, 2020

A curious case of dynamic disorder in pyrrolidine rings elucidated by NMR crystallography

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.

Graphical abstract: A curious case of dynamic disorder in pyrrolidine rings elucidated by NMR crystallography

Supplementary files

Article information

Article type
Communication
Submitted
31 Jul 2020
Accepted
08 Oct 2020
First published
13 Oct 2020
This article is Open Access
Creative Commons BY license

Chem. Commun., 2020,56, 14039-14042

A curious case of dynamic disorder in pyrrolidine rings elucidated by NMR crystallography

P. M. J. Szell, S. P. Brown, L. P. Hughes, H. Blade and S. O. Nilsson Lill, Chem. Commun., 2020, 56, 14039 DOI: 10.1039/D0CC05236A

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