Methylated ammonium compounds classes

Figure 6.2. (Upper panel) The four major classes of organic osmolytes (I) sugars and polyhydric alcohols (polyols) (II) amino acids and amino acid derivatives (III) methylated ammonium and sulfonium compounds and (IV) urea. (Figure modified after Somero and Yancey, 1997.) (Lower panel) Structures of charged osmolytes accumulated in extremely halophilic archaea (after Martin et al., 1999). Note that these osmolytes commonly represent a type of organic osmolyte that is found in many bacteria or eukaryotes to which a charged group has been attached. Typically, the charged group is anionic, for example, a phosphate or a carboxylate group.

The formation of quaternary ammonium salts, followed by an elimination of the kind just described, is very useful in the determination of the structures of certain complicated nitrogen-containing compounds. The compound, which may be a primary, secondary, or tertiary amine, is converted into the quaternary ammonium hydroxide by treatment with excess methyl iodide and silver oxide. The number of methyl groups taken up by nitrogen depends upon the class of the amine a primary amine will take up three methyl groups, a secondary amine will take up two, and a tertiary amine only one. This process is known as exhaustive methylation of amines. 

Initially, tetramethylammonium hydroxide was used [121-124], but tetrabutylammonium hydroxide was better for very voiatile acids [125], and subsequently trimethylanilinium hydroxide (TMAH) was found to be preferable to the tetramethyl compound, and has been widely used as a methylating agent for a variety of different classes of compounds, particularly drugs, but also including acids [120, 126—129]. The w-trifluoro-methyl substituted analogue of TMAH has also been used for free fatty acids and lipid components in biological material, e.g. needle biopsies. This reagent, tri-methyl-(a,a,a-trifluoro-m-tolyl)ammonium hydroxide or TMTFTH, was chosen because it could be used at a... 

Phenoxy acid herbicides, sulfonyl ureas, quaternary ammonium derivatives (quats), and aryloxy propanoic acids are the main classes of compounds subjected to capillary zone electrophoresis (CZE). Triazines are also separated using nonaqueous CZE, while low pfCa characterized chlorotriazines require an ion-pair-like solubilization using cationic surfactants (tetradecylammonium bromide, dodecyltrimethyl-ammonium bromide). Chiral selectors are added in CZE for obtaining enantioselectivity. Chiral selectors used for herbicide enantiomeric discrimination are vancomycin, y-cyclodextrin, ethyl carbonate -cyclo-dextrin, cyclohexyl-alkyl-)S-D-maltoside, sulpropyl ether a-cyclodextrin, and hexakis(2,3-di-0-methyl)-a-cyclodextrin. 

Chemical compatibility/resistance is of particular importance to medical applications. Disinfectants represent one class of chemicals that includes Betadine , glutaraldehyde-based disinfectants, sodium hypochlorite solution (5 %), ethyl alcohol, isopropyl alcohol, hydrogen peroxide (3 %), and ammonium chloride-based disinfectant. Additionally, resistance to methyl ethyl ketone, saline solution, lipid-based compounds, and fatty acids is important. 

Another class of esterification reagents are halogenated compounds (alkyl iodides, substituted benzyl, and phena-cyl bromides), which need basic media for their reaction [K2CO3 or DMFA (dimethyl formamide) is normally used for the neutralization of HHal as acid by-product]. For methy-lation of carboxylic acids, some tetra-substituted ammonium hydroxides or halides can be used, e.g., tetramethylammo-nium hydroxide (in aqueous solutions) or trimethylanilinium hydroxide (in methanol solution). The intermediate ammonium carboxylates are thermally unstable and produce methyl alkanoates when the reaction mixtures are heated or when the carboxylates are introduced into the hot injector of the gas chromatograph (flash or on-column methylation) ... 

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