Polyamines. IV. Spectroscopic properties of N,N-bis-(1,8-naphthalenedicarboximidopropyl)-N-propylamine and supramolecular interactions in its crystals

A new derivative of polyamine, N,N-bis-(1,8-naphthalenedicarboximidopropyl)-N-propylamine has been synthesized and its structure studied by X-ray diffraction, FTIR, 1H and 13 C NMR spectroscopy. The B3LYP and DFT calculations have been carried out. The molecular conformation is folded and stabilized by intramolecular CH⋯O interaction. A close similarity to the conformation of N,N-bis-(phthalimidopropyl)-N-propylamine and N,N-bis-(phthalimidopropyl)-N-octylamine has been found. The supramolecular structure is driven by π⋯π interactions and by weak CH⋯O hydrogen bonds. The optimized bond length as well as bond angles for N,N-bis-(1,8-naphthalenedicarboximidopropyl)-N-propylamine calculated by B3LYP/3-21G approach are compared with the X-ray data. The screening constants for 13C and 1H atoms have been calculated by GIAO/B3LYP/3-21G approach and analyzed. Linear correlation between the experimental 1H and 13C chemical shifts and the computed screening constants have been obtained. Similarly, a linear relationship between the experimental (νexp.) and calculated wavenumbers (νcalc.) for N,N-bis-(1,8-naphthalenedicarboximidopropyl)-N-propylamine has been obtained.