synthesis, molecular structure and spectral properties of quaternary ammonium derivatives of 1,1-dimethyl-1,3-propylenediamine季铵的合成、分子结构和光谱性质的衍生品,1-dimethyl-1 3-propylenediamine.pdf

Molecules 2008, 13, 379-390 molecules ISSN 1420-3049 © 2008 by MDPI /molecules Full Paper Synthesis, Molecular Structure and Spectral Properties of Quaternary Ammonium Derivatives of 1,1-Dimethyl-1,3-propylenediamine Iwona Kowalczyk Laboratory of Microbiocides Chemistry, Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland; E-mail: iwkow@.pl Received: 30 January 2008; in revised form: 12 February 2008 / Accepted: 12 February 2008 / Published: 15 February 2008 Abstract: 1,1-Dimethyl-3-oxo-1,4-diazepan-1-ium chloride (1) and 1,1-dimethyl-1- carboxymethyl-3-aminopropyl ammonium hydrochloride (2) have been obtained by the reactions of 1,1-dimethyl-1,3-propylenediamine with ethyl chloroacetate and chloroacetic acid, respectively. The products have been characterized by FTIR, Raman and NMR spectroscopy. B3LYP calculations have also been carried out. The screening constants for 13C- and 1H- atoms have been calculated by the GIAO/B3LYP/6-31G(d,p) approach and analyzed. The FTIR and NMR spectra of the investigated compounds 1 and 2 are in excellent agreement with the structures optimized by Density Functional Theory (DFT) calculations. Keywords: 1,1-Dimethyl-3-oxo-1,4-diazepinium chloride; 1,1-dimethyl-1-carboxy- methyl-3-aminopropylammonium hydrochloride; FTIR, Raman and NMR spectra; DFT calculations. Introduction Quaternary alkyl ammonium salts (QAC) play an impor