Issue 11, 2015

X-ray studies of conformation: observation of conformational polymorphism of a glycoluril clip

Abstract

In order to study the conformational behavior of a glycoluril clip, compound 1 was synthesized and X-ray crystallography, NMR spectroscopy, and molecular modeling were used in the work. The results of the computational studies revealed the stability of the four conformers retained the order aa > assa > ss in both gas and solvation models, while solvation decreased the relative energies of each conformer dramatically. In the solid phase, X-ray crystallographic analysis indicated that compound 1 presented conformational polymorphism when it crystallized in various solvents. We fortunately obtained a single crystal of the aa and as conformers of the same glycoluril clip. The X-ray crystallographic analysis in this report provides the first crystallographic evidence of the conformers of a glycoluril clip. Unlike in the solid state, the conformers interconvert rapidly in solution and therefore cannot be detected on the NMR timescale.

Graphical abstract: X-ray studies of conformation: observation of conformational polymorphism of a glycoluril clip

Supplementary files

Article information

Article type
Communication
Submitted
12 Jan 2015
Accepted
02 Feb 2015
First published
04 Feb 2015

CrystEngComm, 2015,17, 2245-2249

Author version available

X-ray studies of conformation: observation of conformational polymorphism of a glycoluril clip

J. Wang, Y. Gao, J. Xiang, M. Wang and A. Wu, CrystEngComm, 2015, 17, 2245 DOI: 10.1039/C5CE00066A

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