Polyamines. III. Spectroscopic properties of N,N-bis-(phthalimidopropyl)-N-octylamine and supramolecular interactions in its crystals
[ 1 ] Instytut Chemii i Elektrochemii Technicznej, Wydział Technologii Chemicznej, Politechnika Poznańska | [ P ] employee
2010
scientific article
english
- N.N-bis-(phthalimidopropyl)-N-octylamine
- X-ray diffraction
- B3LYP calculations
- FTIR and NMR spectra
- Supramolecular structure
EN A new derivative of polyamine, N,N-bis-(phthalimidopropyl)-N-octylamine has been synthesized and its structure studied by X-ray diffraction, FTIR, 1H and 13C NMR spectroscopy. The B3LYP and DFT calculations have been carried out. The molecular conformation of N,N-bis-(phthalimidopropyl)-N-octylamine is folded and stabilized by an intramolecular CAH O hydrogen bond. A close similarity to the conformation of N,N-bis-(phthalimidopropyl)-N-propylamine has been found. The both molecules differ by the length of the saturated chains on the N-amine atom. The long N-octyl chain substituent gives rise to the supramolecular structure which is different to that one formed by the N-propyl derivative. The supramolecular structure is driven by weak CAH O and p p interactions. The optimized bond lengths as well as bond angles for N,N-bis-(phthalimidopropyl)-N-octylamine calculated by B3LYP/6-31G(d,p) approach are compared with the X-ray data. The screening constants for 13C and 1H atoms have been calculated by the GIAO/B3LYP/6-31G(d,p) approach and analyzed. Linear correlations between the experimental 1H and 13C chemical shifts and the computed screening constants have been obtained.
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