Ammonium compounds, substituted salts

Ammonium Compounds. Salts and hydroxides containing quadricovalent nitrogen are named as a substituted ammonium salt or hydroxide. The names of the substituting radicals precede the word ammonium, and then the name of the anion is added as a separate word. For example, (CH3)4N+I is tetramethylammonium iodide. 

Quaternary ammonium compounds are usually named as the substituted ammonium salt. The anion is Hsted last (3). Substituent names can be either common (stearyl) or lUPAC (octadecyl). If the long chain in the compound is from a natural mixture, the chain is named after that mixture, eg, taHowalkyL Prefixes such as di- and tri- are used if an alkyl group is repeated. Complex compounds usually have the substituents Hsted in alphabetical order. Some common quaternary ammonium compounds and their appHcations in patent Hterature are Hsted in Table 1. 

The isomeric optically active substituted ammonium salts which have been reported by organic chemists are not readily explained by an ammonium theory such as has been wrongly assumed to have been established by the experiments of V. Meyer and M. T. Lecco—vide supra. J. C. Cain argued from the above hypothesis of the constitution of the ammonium compounds that the optical activity is the result of a similar spatial configuration as that assumed for the carbon compounds where the quadrivalent nucleus, say NCI", instead of quadrivalent carbon, is at the centre of a tetrahedron so that... 

Crown ethers of the type discussed in this section have been used as sensors, membranes, or materials for chromatography. Shinkai used cholesterol-substituted crown ether 10 as a sensor for chirality in chiral ammonium compounds (Scheme 16). It was found that the pitch of the cholesteric phase exhibited by 10 was changed upon addition of the chiral salt. As the wavelength of reflection for incident light depends on the pitch, a color change was observed that was visible to the naked eye [45, 46]. Such chirality sensing systems were known before but chromophores had to be bound to the crown ether in order to observe color changes [47]. This problem could be overcome by 10, which uses intrinsic properties of the chiral nematic phase. 

Quaternary compounds (substituted ammonium salts, methacholine chloride, mepenzolate bromide, phospholine iodide, etc.) approximately 10%... 

Most nonmetal borates reported in the literature are ammonium and substituted ammonium salts, hi general, boric acid forms salts with alkyl- or aryl-amines that are roughly as or more basic than pyridine. Depending on the reaction conditions, a number of different crystalline borates might be isolated from a given amine. However, the chemistry of substituted amine borates is dominated by the occurrence of pentaborates, and relatively few compounds in this class have been reported containing more basic borates anions. 

Regarding titrants, cationic substances (for example, protonized alkaloids, compounds containing quaternary nitrogen, etc.) are usually titrated with sodium tetraphenylborate, the exact concentration of which is determined titrimetrically against a standard substance such as thallium(I) nitrate or pure copper(II) or nickel(II) salts in the presence of 1,10-phenanthroline. For titrations of anionics, substituted quaternary ammonium or pyridinium salts are applied. The procedures are simple and represent an ecologic alternative to so-called two-phase titrations. ... 

Reactivity follows the sequence RI > RBr > RC1, and SnL > SnBr2 > SnCl2. The uncatalysed reaction of methyl iodide with stannous iodide at 160 °C has been reported,72 but usually a catalyst is necessary. These catalysts are similar to those which are used for the direct reactions, and include dialkyl sulphides, amines, ammonium and phosphonium salts, and copper(II). The trialkylstibines appear to be particularly effective and the compounds RSnX3, R = Ci to Cis, have been prepared by this method. A similar reaction with the a,co-dihalides, X(CH2) X, n = 4-5, provides access to functionally substituted tetraorganotin compounds, but the aryl halides are unreactive. 

They are soluble in water, show a strong alkaline reaction like the sulphonium and ammonium compounds, and give with halogen hydradds predpitates of the corresponding salts. If the dried salts be heated, they decompose into two molecules of the hydrocarbon substitution product, e.g. ... 

Basic carriers (Table 27.1) consist mainly of amine-based compounds such as quaternary ammonium salts (e.g., Aliquat 336), tertiary amines (e.g., tri-n-octylamine [TOA], tri-isooctylamine [TlOA]), weakly basic compounds (e.g., alkyl derivatives of pyridine N oxides), and thiadiazine derivatives (e.g., 5-(4-phenoxyphenyl)-6/f-l,3,4-thiadiazin-2-amine [FFAT]). The reason for this classification is related to the similarity in the extraction mechanism involving the carriers discussed. In the case of fully substituted quaternary ammonium compounds (e.g., Aliquat 336), the carrier reacts as an anion exchanger forming an ion-pair with another anion from the feed phase, which can be a complex metal anion. In the case of amine and other weak bases mentioned earlier, the carrier must be protonated first in order to allow anion exchange with another anion from the feed phase or with a complex metal anion. Alternatively, the carrier may react directly with a protonated complex metal anion [16]. 

Another group of seven water soluble initiators is based on methyl substituted salts, 3 -(9-oxo-9H-thioxanthene-2-yloxy)-N,N,N-trimethylpropane ammonium. These compounds are both water and isopropyl alcohol soluble. ... 

Another organosulfur compound that is used as a herbicide for certain kinds of weed and in nickel electroplating is ammonium sulfamate, the salt of amino-sulfonic acid. Sulfamate is also one of the degradation products of topiramate (2,3 4,5-bis-0-methylethylidene-fi-D-ffuctopyranose sulfamate) that is a sulfa-mate-substituted monosaccharide. 

Melamine-formaldehyde resins can be cured with substituted ammonium compounds. Silicone resins can be catalysed with cobalt octoate or naphthenate or with the corresponding salts of zinc, iron or lead. Polyurethanes can be cured with isocyanates. 

Generally the desired substituted carbonyl compound 3 is obtained after hydrolytic workup under acidic conditions. With simple alkyl halides an irreversible A-alkylation may take place as a side-reaction to give a quaternary ammonium salt 7 ... 

Quaternary ammonium salts are organically substituted nitrogen compounds in which the nitrogen atom is pentavalent. Four of the substituents are alkyl, aryl or heterocyclic radicals and the fifth is an anion (a cationic charge). This anion is mostly chloride. Therefore we call them benzalkonium chlorides. 

Mixed condensation of 4-sulfophthalic acid with other substituted phthalic acids (typically >200 °C, metal salt, urea, ammonium molybdate catalyst Figure 6) again gives mixtures.246-248 Routes which lead predominantly to monosulfonic acids of zinc(II) phthalocyanine and related compounds have been described.247,250... 

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