Premium
The behavior of Gliclazide in solution and in the solid state: a case of organic compound presenting a solid‐solution structure
Author(s) -
Santa María Dolores,
Claramunt Rosa M.,
Alkorta Ibon,
Elguero José
Publication year - 2009
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2414
Subject(s) - chemistry , solid state , gliclazide , solid solution , solid state nuclear magnetic resonance , pyrrolidine , crystal structure , sulfonamide , crystallography , stereochemistry , organic chemistry , nuclear magnetic resonance , medicine , physics , insulin , endocrinology
The structure of the hypoglycemic agent Gliclazide has been studied by 1 H, 13 C, and 15 N NMR in solution (CDCl 3 and DMSO‐ d 6 ) and in the solid state. In the solid state, the compound crystallizes as an EZ isomer without dynamic properties. In CDCl 3 solution, the structure is still EZ but with a slow nitrogen inversion about the pyrrolidine nitrogen: two invertomers have been observed and characterized. In DMSO‐ d 6 , the rate is faster and only averaged signals were observed. GIAO calculated absolute shieldings were used to confirm the nature of the observed species. In the solid state, Gliclazide presents the phenomenon of solid‐solution with two disordered conformations present in the crystal at a 90:10 ratio. Copyright © 2009 John Wiley & Sons, Ltd.