Title

Solid-State Nmr Characterization Of The Molecular Conformation In Disordered Methyl Α- L -Rhamnofuranoside

Abstract

A combination of solid-state 13C NMR tensor data and DFT computational methods is utilized to predict the conformation in disordered methyl α-l-rhamnofuranoside. This previously uncharacterized solid is found to be crystalline and consists of at least six distinct conformations that exchange on the kHz time scale. A total of 66 model structures were evaluated, and six were identified as being consistent with experimental 13C NMR data. All feasible structures have very similar carbon and oxygen positions and differ most significantly in OH hydrogen orientations. A concerted rearrangement of OH hydrogens is proposed to account for the observed dynamic disorder. This rearrangement is accompanied by smaller changes in ring conformation and is slow enough to be observed on the NMR time scale due to severe steric crowding among ring substituents. The relatively minor differences in non-hydrogen atom positions in the final structures suggest that characterization of a complete crystal structure by X-ray powder diffraction may be feasible. © 2013 American Chemical Society.

Publication Date

7-3-2013

Publication Title

Journal of Physical Chemistry A

Volume

117

Issue

26

Number of Pages

5534-5541

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/jp4036666

Socpus ID

84879765478 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/84879765478

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