Abstract
The crystal structure, at 120 K, and solution H-1 and C-13 NMR spectra of ethyl 1,2,3,4-tetra-O-acetyl-beta-D- glucopyranuronate, (8) have been determined. Compound 8 crystallizes in the triclinic space group, P1(Z = 1) with a = 6.0209(3) Angstrom, b = 8.9698(5) Angstrom, c = 9.9818(8) Angstrom, alpha = 104.965(2)degrees, beta = 98.522(3)degrees, gamma = 106.790(5)degrees. The Cremer and Pople puckering parameters [Q = 0.602(4) Angstrom, theta = 7.1(4)degrees, phi = 325(3)degrees] for the pyranose ring in the solid state indicate a near ideal C-4(1) chair conformation with a slight distortion in the direction towards H-0(5). A number of weak, soft intermolecular C-H...O hydrogen bonds set up a 3D array. NMR spectra and FAB and EIMS data have been obtained. Solution NMR parameters suggest that the solid state conformation is maintained in solution in chloroform.
| Original language | English |
|---|---|
| Pages (from-to) | 33-38 |
| Number of pages | 6 |
| Journal | Journal of Chemical Crystallography |
| Volume | 33 |
| Publication status | Published - 2003 |
Keywords
- glucopyranuronic derivatives
- conformation
- NMR
- MS
- X-ray-diffraction
- hydrogen-bond