Strategies for the Synthesis of N-Arylammonium Salts

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3535-3545 ◽  
Author(s):  
Charles Diesendruck ◽  
Shlomy Arava
Keyword(s):  
Organic Chemistry ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Tertiary Amines ◽  
Pyrylium Salts ◽  
Menshutkin Reaction ◽  
Nucleophilic Aromatic Substitutions ◽  
Ammonium Compounds ◽  
General Method

The N-arylation of tertiary amines to provide sp3 quaternary ammonium salts is a challenge in organic chemistry. To date, no general method for such arylations has been established. Here, we summarize a variety of strategies that have been tested, starting with harsh nucleophilic aromatic substitutions, through to the use of copper catalysis and the application of strong electrophiles, such as phenyl cations and benzynes. The achievements and limitations of each method are summarized, and the challenges yet to be met in the synthesis of charged ammonium compounds are described.1 Introduction2 Alkylation of Anilines: The Menshutkin Reaction3 Arylations3.1 Nucleophilic Aromatic Substitutions by Tertiary Amines3.2 Preparation of N-Arylpyridinum Salts from Zincke and Pyrylium Salts3.3 Arylations Using Phenyl Cations3.4 Copper-Catalyzed Arylation of N-Heteroarenes3.5 Benzynes as Aryl Electrophiles4 Conclusions and Perspective

scholarly journals Biological Evaluation of Quaternary bis Ammonium Salt and Cetylpyridinum Bromide Against S. epidermidis biofilm

2013 ◽  
Vol 62 (4) ◽  
pp. 359-364
Author(s):  
Justyna Stefańska ◽  
Anna Pietruczuk-Padzik ◽  
Marta Struga ◽  
Maciej Borkowski ◽  
Stefan Tyski
Keyword(s):  
Ammonium Salt ◽  
Broad Spectrum ◽  
Quaternary Ammonium ◽  
Biological Evaluation ◽  
Quaternary Ammonium Compounds ◽  
Quaternary Ammonium Salts ◽  
Bacterial Biofilm ◽  
Ammonium Salts ◽  
Ammonium Compounds

Quaternary ammonium compounds are broad-spectrum bacteriocides widely used as antiseptics, disinfection and preservation agents. The aim of this study was to examine the activity of two quaternary ammonium salts, cetylpyridinum bromide and a newly synthesized quaternary bis ammonium salt, against S. epidermidis biofilm. The average values of killing efficiency for cetylpyridinum bromide ranged from 26.6% to 64.1% for all tested concentrations (0.125 to 8.0 microg x mL(-1)) and for quaternary bis ammonium salt the percentage of killing efficiency ranged from 59.7% to 88.4% for tested concentrations (from 2.0 to 128.0 microg x mL(-1)). Both tested compounds significantly affect staphylococcal biofilms, but any of used concentrations caused a total eradication of bacterial biofilm.

scholarly journals Synthesis and Surfactant Studies of Dialkyl Dimethyl Quaternary Ammonium Bromide Formulations

2006 ◽  
Vol 5 (3) ◽  
Author(s):  
Rocky Barney ◽  
Tony Stark ◽  
Dru Delaet
Keyword(s):  
Quaternary Ammonium ◽  
Carbon Chain ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Ammonium Bromide ◽  
Tertiary Amines ◽  
Alkyl Bromide ◽  
Component Systems ◽  
Multiple Component ◽  
Chain Lengths

Quaternary ammonium salts (otherwise known as quats) are commonly used active ingredients in biocide formulations used in the anti-microbial industry. Although quats have been established to be effective biocides, there are few studies investigating the maximization of biocidal efficacy in multiple component formulations using various carbon chain lengths. Reported here is the synthesis based on the Sn2 reaction of tertiary amines with alkyl bromide. Surfactant studies of the single and dual component systems were conducted, and the evaluation is explored.

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