Polyphosphoric acid catalyzed cyclization of aralkenyl-substituted quaternary ammonium salts

Venkataramu, S. D.; Macdonell, G. D.; Purdum, W. R.; Dilbeck, G. A.; Berlin, K. Darrell

doi:10.1021/jo00433a001

Cited by 13 publications

(4 citation statements)

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“…One of the new groups with good antimicrobial activity are cyclic quaternary ammonium salts [ 3 ]. Some cyclic quaternary ammonium salts have been obtained previously by intramolecular cyclisation of amine derivatives [ 4 , 5 , 6 , 7 , 8 , 9 ]. Another way, i.e., reaction of alkyl halides with cyclic amines can lead to chiral cyclic quaternary ammonium salts [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Structure, Spectral Properties and Antifungal Activity of Polymethylene-α,ω-bis(N,N- dimethyl-N-dodecyloammonium Bromides)

2011

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Hexamethylene-1,6-bis-(N,N-dimethyl-N-dodecylammonium bromide) (1), pentamethylene-1,5-bis(N,N-dimethyl-N-dodecylammonium bromide) (2), tetramethylene-1,4-bis(N,N-dimethyl-N-dodecylammonium bromide) (3), trimethylene-1,3-bis(N,N-dimethyl-N-dodecylammonium bromide) (4) and ethylene-1,2-bis(N,N-dimethyl-N-dodecylammonium bromide) (5) 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 Hartree-Fock/3-21G(d,p) approach have been presented. MIC values for A. niger, P. chrysogenum, C. albicans have been determined and the relationship between MIC and spacer length has been discussed.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Structure, Spectral Properties and Antifungal Activity of Polymethylene-α,ω-bis(N,N- dimethyl-N-dodecyloammonium Bromides)

2011

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“…not determined;l iquid at room temperature. 1 N-Allyl-N,N-diethylbenzenaminium bromide (1 e-Br) [31] Diethylaniline (0.48 mL, 3.0 mmol) and allyl bromide (0.78 mL, 9.0 mmol) were combined and kept stirring at 50 8Cf or 48 h. The white solid was precipitated then washed with diethyl ether. N-Allyl-N,N-dimethylbenzenaminium hexafluorophosphate (1 a-PF 6 ).…”

Section: General Procedures For Kinetic and Thermodynamic Measurement mentioning

confidence: 99%

“…Prepared in 80 %y ield as aw hite solid by ar oute analogous to that described for 1a-PF 6 N,N,N-Triethylprop-2-en-1-aminium bromide(3a-Br) [32,33] Prepared in 92 %yield as awhite hygroscopic solid by aroute analogous to that described for 1a-Br. 1 N-Benzyl-N,N-dimethylprop-2-en-1-aminium bromide (3 c-Br) [31] Prepared in 30 %yield as awhite hygroscopic solid by aroute analogous to that described for 1a-Br. 1 N,N-Diethyl-N-(2-hydroxyethyl)prop-2-en-1-aminium bromide (3 d-Br) [34] Prepared in 72 %y ield as aw hite solid by ar oute analogous to that described for 1a-Br.…”

Section: General Procedures For Kinetic and Thermodynamic Measurement mentioning

confidence: 99%

Dynamic Covalent Chemistry of Nucleophilic Substitution Component Exchange of Quaternary Ammonium Salts

Kulchat

Lehn

2015

Chemistry An Asian Journal

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Dynamic covalent libraries (DCLs) of quaternary ammonium cations were set up by reversible nucleophilic substitution (S(N)2' and S(N)2) exchange reactions of ammonium salts and tertiary amines. The reactions were conducted at 60 °C to generate thermodynamically and kinetically controlled mixtures of quaternary ammonium compounds and tertiary amines, and were accelerated by using iodide as a nucleophilic catalyst. Microwave irradiation was used to assist the exchange reaction between the pyridinium salts and pyridine derivatives. Finally, experiments towards the generation of dynamic ionic liquids were performed. The results of this study pave the way for the extension of dynamic combinatorial chemistry to nucleophilic substitution reactions.

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“…N,N -dioctyl-azepanium, N,N -dioctylpiperidinium and N,N -dioctylpyrrolidinium bromides, with potential antimicrobial activity. Some cyclic quaternary ammonium salts have previously been obtained by intramolecular cyclisation of amine derivatives [ 4 , 5 , 6 , 7 , 8 , 9 ]. Another way, i.e.…”

Section: Introductionmentioning

confidence: 99%

Study of Cyclic Quaternary Ammonium Bromides by B3LYP Calculations, NMR and FTIR Spectroscopies

2010

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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.

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Polyphosphoric acid catalyzed cyclization of aralkenyl-substituted quaternary ammonium salts

Cited by 13 publications

References 1 publication

Synthesis, Molecular Structure, Spectral Properties and Antifungal Activity of Polymethylene-α,ω-bis(N,N- dimethyl-N-dodecyloammonium Bromides)

Synthesis, Molecular Structure, Spectral Properties and Antifungal Activity of Polymethylene-α,ω-bis(N,N- dimethyl-N-dodecyloammonium Bromides)

Dynamic Covalent Chemistry of Nucleophilic Substitution Component Exchange of Quaternary Ammonium Salts

Study of Cyclic Quaternary Ammonium Bromides by B3LYP Calculations, NMR and FTIR Spectroscopies

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