Study of N, N-dimethyl(carboethoxymethyl)-3-phthalimidopropylammonium chloride dihydrate by DFT calculations, NMR and FTIR spectroscopy

Abstract

N, N-dimethyl(carboethoxymethyl)-3-phthalimidopropylammonium chloride dihydrate ( 1) and N, N-dimethyl(carboxymethyl)-3-phthalimidopropylammonium hydrochloride ( 3) have been obtained in reaction of N, N-dimethyl-3-phthalimidopropylamine with ethyl chloroacetate and chloroacetic acid, respectively. N, N-dimethyl(carboethoxymethyl)-3-phthalimido-propylammonium chloride dihydrate ( 1) has been characterized by FTIR and NMR spectroscopy. Moreover, for ( 1) and ( 3) B3LYP calculations have been carried out. The optimized bond lengths, bond angles and torsion angles calculated by B3LYP/6-31G(d,p) approach have been presented. Both FTIR and Raman spectra of ( 1) are consistent with the calculated structures in the gas phase. Correlations between the experimental 1H and 13C NMR chemical shifts ( δ exp) of investigated compound in D 2O, and the GIAO/B3LYP/6-31G(d,p) calculated magnetic isotropic shielding tensors ( σ calc), δ exp = a + b σ calc, are reported. The assignments of the anharmonic experimental solid state vibrational frequencies of ( 1) based on the calculated B3LYP/6-31G(d,p) harmonic frequencies have been made. Linear correlations between the experimental 1H and 13C chemical shifts and the computed screening constants confirm the optimized geometry.