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 Original Research Article

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.