Polyamines - V: The structure of tetramethylene-1,4-bis(N-deoxyglucitolammonium chloride) studied by X-ray diffraction, DFT calculations, NMR and FTIR spectroscopy

A new derivative of polyamine, tetramethylene-1,4-bis(N-deoxyglucitolammonium chloride) (4), has been synthesized and its structure studied by X-ray diffraction, DFT calculations, solid state FTIR and and C-13 NMR spectroscopy in D2O. The dication of (4), in the shape of a very flattened bow, adopts fully extended planar conformation that is stabilized by N+-H center dot center dot center dot-Cl- and O-H center dot center dot center dot O intermolecular hydrogen bonds. The whole dication occupies the special position on a twofold axis of symmetry. The magnetic isotropic shielding constants, sigma(calc), were calculated by the GIAO/B3LYP/6-31 G(d,p) approach and linear correlations with H-1 and C-13 chemical shifts were obtained. The effects of hydrogen bonding and electrostatic interactions on the structure of tetramethylene-1,4-bis(N-deoxyglucitolammonium chloride) (4), in the crystal and in the isolated molecule have been discussed. (C) 2012 Elsevier B.V. All rights reserved.