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

The X-ray diffraction analysis of N-(methyl 3,4,6-tri-O-acetyl-alpha -D-glucopyranosid-2-yl)-N'-p-chlorophenyloxamide (1), N-(methyl 3,4,6-tri-O-acetyl-alpha -D-glucopyranosid-2-yl)-N',N'-diethyloxamide (2), N-acetyl, N-(methyl 3,4,6-tri-O-acetyl-beta -D-glucopyranosid-2-yl), N'-methyl, N'-phenyloxamide (3), N-acetyl, N-(methyl 3,4,6-tri-O-acetyl-beta -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 pi 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. (C) 2001 Elsevier Science Ltd.. All rights reserved.