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

Abstract 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, 1 H and 13 C NMR spectroscopy. The B3LYP and DFT calculations have been carried out. The molecular conformation is folded and stabilized by intramolecular C H⋯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 C H⋯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 13 C and 1 H atoms have been calculated by GIAO/B3LYP/3-21G approach and analyzed. Linear correlation between the experimental 1 H and 13 C chemical shifts and the computed screening constants have been obtained. Similarly, a linear relationship between the experimental ( ν exp. ) and calculated wavenumbers ( ν calc. ) for N , N -bis-(1,8-naphthalenedicarboximidopropyl)- N -propylamine has been obtained.