Synthesis, characterization, and crystal structure of α-glucosimino- pyranose anthranilic acid

Abstract

The new secondary amine, build of glucose and anthranilic acid - α-glucosiminopyranose anthranilic acid (1) - has been synthesized and characterized by elemental analyses, FT-IR and 1H NMR spectroscopy. Crystal and molecular structure of the hydrate of 1 has been determined by means of X-ray diffraction. 1·H2O crystallizes in monoclinic P21 space group, with a = 15.584(3) Å, b = 4.992(1) Å, c = 18.928(4) and β = 107.63(3)°. The studies prove that a cyclic secondary amine is formed instead of open chain Schiff base, and only one anomer, α is produced. There are two symmetry-independent molecules of 1·H2O in the asymmetric part of the unit cell, and these independent molecules create complicated hydrogen bonded structures - starting with the homomolecular chains which in turn are joined into three dimensional structure. The differences in the supramolecular structures are correlated with the differences in the bond angles patterns, which result from the different orientations of certain O-H bonds. The antibacterial activities of 1 were also tested but the results were negative. © 2012 The Author(s).