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Synthesis, characterisation and crystal structures of Schiff bases from the reaction of 4,6-O-ethylidene-β-D-glucopyranosylamine with substituted salicylaldehydes

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Title Synthesis, characterisation and crystal structures of Schiff bases from the reaction of 4,6-O-ethylidene-β-D-glucopyranosylamine with substituted salicylaldehydes
 
Creator SAH, AJAY K
RAO, CHEBROLU P
SAARENKETO, PAULI K
KOLEHMAINEN, ERKKI
KARI RISSANEN
 
Subject crystal structure
glucose
nuclear magnetic resonance
organic compounds
solubility
solvents
 
Description Multiple chemical modifications were carried out on D-glucose to result in the corresponding Schiff bases. Such modifications performed on D-glucose not only helped in increasing the solubility of the products in nonaqueous solvents, but also restricted the anomerisation of the saccharide moiety in solution. NMR study of the products revealed the presence of the β-anomeric form of the saccharide moiety in Me2SO solution. All the compounds were characterised by analytical and spectral methods. The literature is devoid of any crystal structures of saccharide–Schiff base combinations of the type reported in this paper. The crystal structures of these molecules exhibited a tridentate, ONO binding core. These studies further revealed that the compounds in the solid state were in the β-D-pyranose form with the 4C1 chair conformation. The compounds exhibited interesting lattice structures assisted through weak interactions of the type O–H...O and C–H...O. The lattice structure of one of these compounds exhibited channels filled with chloroform molecules.
 
Publisher Elsevier
 
Date 2009-03-02T09:29:56Z
2011-11-25T18:20:07Z
2011-12-26T13:06:30Z
2011-12-27T05:54:20Z
2009-03-02T09:29:56Z
2011-11-25T18:20:07Z
2011-12-26T13:06:30Z
2011-12-27T05:54:20Z
2001
 
Type Article
 
Identifier Carbohydrate Research 335(1), 33-43
0008-6215
http://dx.doi.org/10.1016/S0008-6215(01)00201-4
http://hdl.handle.net/10054/838
http://dspace.library.iitb.ac.in/xmlui/handle/10054/838
 
Language en