Crystal structure and solid state 13C NMR analysis of N-(methyl 3,4,6-tri-O-acetyl-alpha, and beta-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.
Temeriusz
A
A
Department of Chemistry, Warsaw University, Pasteura 1, PL-02-093, Warsaw, Poland. atemer@chem.uw.edu.pl
Anulewicz
R
R
Wawer
I
I
Krygowski
T M
TM
Piekarska-Bartoszewicz
B
B
Rowińska
M
M
D000814:Aniline Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray / Q000379:methods; D015394:Molecular Structure; D008970:Molecular Weight; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D010072:Oxamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*
D000814:Aniline Compounds; D010072:Oxamic Acid