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 1H and 13C 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⋯Cl− and O–H⋯O intermolecular hydrogen bonds. The whole dication occupies the special position on a twofold axis of symmetry. The magnetic isotropic shielding constants, σcalc, were calculated by the GIAO/B3LYP/6-31 G(d,p) approach and linear correlations with 1H and 13C 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.

► X-Ray, DFT, FTIR, NMR of tetramethylene-1,4-bis(N-deoxyglucitolammonium chloride).
► The molecular structure is stabilized by hydrogen bonds and electrostatic interactions.
► In crystal the chloride anion interact with hydroxyl hydrogen atom (O(5)H).