Study of Cyclic Quaternary Ammonium Bromides by B3LYP Calculations, NMR and FTIR Spectroscopies 英文参考文献.docVIP

Molecules 2010, 15, 5644-5657; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Study of Cyclic Quaternary Ammonium Bromides by B3LYP Calculations, NMR and FTIR Spectroscopies Bogumi? Brycki *, Adrianna Szulc and Iwona Kowalczyk Laboratory of Microbiocides Chemistry, Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland; E-Mails: iwkow@.pl (I.K.); adrszu@ (A.S.) * Author to whom correspondence should be addressed; E-Mail: brycki@.pl. Received: 26 July 2010; in revised form: 11 August 2010 / Accepted: 13 August 2010 / Published: 16 August 2010 Abstract: N,N-dioctyl-azepanium, -piperidinium and -pyrrolidinium bromides 1-3, have been obtained and characterized by FTIR and NMR spectroscopy. DFT calculations have also 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 1-3 are consistent with the calculated structures in the gas phase. 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 confirm the optimized geometry. Keywords: N,N-dioctyl-azepanium; -piperidinium; -pyrrolidinium bromides; DFT calculations; FTIR and NMR spectra 1. Introduction Quaternary ammonium compounds (QACs) were introduced as antimicrobial agents by Domagk over seventy years ago [1]. The first generation of QACs were standard benzalkonium chlorides, i.e. alkylbenzyldimethylammonium chloride, with specific alkyl distributions, i.e., C12, 40%; C14, 50% and C16, 10% [2]. The second generation of QACs was obtained by substitution of the aromatic ring in alkylbenzyldimethylammonium chlorides by chlorine or alkyl groups to get products l