Crystal structure and solid state 13C NMR analysis of N-(methyl 3,4,6-tri- O-acetyl-α, and β- d-glucopyranosid-2-yl)-oxamide derivative of p-chloroaniline, N, N-diethylamine, N-methylaniline and N-ethylaniline

• Published in: Carbohydrate research 2001-08, Vol.334 (1), p.71-79
• Main Authors: Temeriusz, Andrzej, Anulewicz, Romana, Wawer, Iwona, Krygowski, Tadeusz M, Piekarska-Bartoszewicz, Bogusława, Rowińska, Magdalena
• Format: Article
• Language: English
• Subjects: 13C NMR analysis; Aniline Compounds - chemistry; Crystal structure; Crystallography, X-Ray - methods; Molecular Structure; Molecular Weight; Nuclear Magnetic Resonance, Biomolecular - methods; Oxamic Acid - analogs & derivatives; Oxamic Acid - chemistry; X-ray diffraction analysis
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(01)00160-4

The X-ray diffraction analysis of N-(methyl 3,4,6-tri- O-acetyl-α- d-glucopyranosid-2-yl)- N′- p-chlorophenyloxamide ( 1), N-(methyl 3,4,6-tri- O-acetyl-α- d-glucopyranosid-2-yl)- N′, N′-diethyloxamide ( 2), N-acetyl, N-(methyl 3,4,6-tri- O-acetyl-β- d-glucopyranosid-2-yl), N′ -methyl, N′-phenyloxamide ( 3), N-acetyl, N-(methyl 3,4,6-tri- O-acetyl-β- d-glucopyranosid-2-yl), N′ -ethyl, N′-phenyloxamide ( 4) was performed. It was found that the oxamide group in compounds 1– 4 can be characterized as two structurally independent amides because there is no π conjugation across the oxalyl OCCO bond. Only the oxamide group of 1 is planar and adopts trans conformation stabilized as two intramolecular NH⋯O hydrogen bonds. Graphic