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Conformation of glyburide in the solid state and in solution

✍ Scribed by Stephen R. Byrn; Ann T. McKenzie; Mahmoud M. A. Hassan; Abdullah A. Al-Badr

Publisher: John Wiley and Sons
Year: 1986
Tongue: English
Weight: 447 KB
Volume: 75
Category: Article
ISSN: 0022-3549
DOI: 10.1002/jps.2600750615

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✦ Synopsis

Nuclear magnetic resonance spectroscopy was combined with X-ray crystallography to determine the solution and solid-state conformations of glyburide (C23H28ClN305S). In solution, there is apparently free rotation about several of the single bonds. Crystals of glyburide belong to space group P2,ln with a = 9.414(3 A, b = 17.591(5)A, c = 14.410(4)A, fl = 93.42(3)", V = 2382(1)a3, R = 0.0694, Z = 4. In the solid, the conformation about all of the bonds is frozen. The torsion angles about some of the important bonds are: C(7)-N(B)-C(9)-C(lO), -86"; N(8)4(9)-C(lO)-C(l l), -179" (extended); S(17)-N(18)-C(19)-N(20), 178" (extended); and N(18)-C( 19)-N(20)-C( 21), -179" (extended). Thus, except for the N(8)-C(9) bond, the conformation in the solid state is extended. The solution and solid-state NMR spectra are different as might be expected based on the differences in conformation discussed above.

4.

On spin-spin decoupling of the CH2 methylene quartet at 6 3.6 ppm, the benzylic methylene triplet at 6 2.9 ppm 596

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