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

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 (δexp) of investigated compound in D2O, and the GIAO/B3LYP/6-31G(d,p) calculated magnetic isotropic shielding tensors (σcalc), δexp = a + b σcalc, 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.