Quaternary ammoniums

Girard s reagents Quaternary ammonium salts of the type Me3NCH2CONHNH2 X which form water-soluble compounds with aldehydes and ketones, and are therefore separable from other neutral compounds the aldehyde or ketone may be subsequently regenerated after separation. 

Pashley R M, McGuiggan P M, Ninham B W, Brady J and Evans D F 1986 Direct measurements of surface forces between bilayers of double-chained quaternary ammonium acetate and bromide surfactants J. Phys. Chem. 90 1637-42... 

In general, the first step in virtual screening is the filtering by the application of Lipinski s Rule of Five [20]. Lipinski s work was based on the results of profiling the calculated physical property data in a set of 2245 compounds chosen from the World Drug Index. Polymers, peptides, quaternary ammonium, and phosphates were removed from this data set. Statistical analysis of this data set showed that approximately 90% of the remaining compounds had ... 

Members of Classes (i), (ii) and (iv) usually react readily with methyl iodide to give methiodides, i.e., quaternary ammonium iodides. 

Methiodides. Methyl iodide reacts with tertiary amines to form the crystalline quaternary ammonium iodide (methiodide) ... 

From ehloromethyl or bromomethyl aromatic compounds by heating with hexamethylenetetramine (hexamine) in aqueous alcohol or aqueous acetic acid. A quaternary ammonium compound is formed, which yields the aldehyde upon treatment with water in the presence of hexamine for example... 

Anion exchange resins of the quaternary ammonium hydroxide type (e.g., De-Acidlte FF, IRA-400 or Dowex I) are strong bases and are useful cataly s for the cyanoethylatlon of alcohols and possibly of other active hydrogen compounds. 

Girard s reagent T is carbohydrazidomethyltrimethylammonium chloride (I) and is prepared by the reaction of the quaternary ammonium salt formed from ethyl chloroacetate and trimethylamine with hydrazine hydrate in alco-hoUc solution ... 

Amines are powerful nucleophiles which react under neutral or slightly basic conditions with several electron-accepting carbon reagents. The reaction of alkyl halides with amines is useful for the preparation of tertiary amines or quaternary ammonium salts. The conversion of primary amines into secondary amines is usually not feasible since the secondary amine tends towards further alkylation. 

Allylic amine is a less reactive leaving group[7], but the allylic ammonium salts 214 (quaternary ammonium salts) can be used for allylalion(l30,131]. Allylic sulfonium salts are also used for the allylation[130]. The allylic nitrile in the cyclic aminonitrile 215 can be displaced probably via x-allylic complex formation. The possibility of the formation of the dihydropyridinium salts 216 and subsequent conjugate addition are less likelyfl 32],... 

Benzyltnmethyl ammonium iodide (a quaternary ammonium salt)... 

Ammonium salts that have four alkyl groups bonded to nitrogen are called quaternary ammonium salts... 

In spite of being ionic many quaternary ammonium salts dissolve m nonpolar media The four alkyl groups attached to nitrogen shield its positive charge and impart lipophilic character to the tetraalkylammonium ion The following two quaternary ammonium salts for example are soluble m solvents of low polarity such as benzene decane and halo genated hydrocarbons... 

This property of quaternary ammonium salts is used to advantage m an experi mental technique known as phase transfer catalysis Imagine that you wish to carry out the reaction... 

Sodium cyanide does not dissolve m butyl bromide The two reactants contact each other only at the surface of the solid sodium cyanide and the rate of reaction under these con ditions IS too slow to be of synthetic value Dissolving the sodium cyanide m water is of little help because butyl bromide is not soluble m water and reaction can occur only at the interface between the two phases Adding a small amount of benzyltrimethyl ammonium chlonde however causes pentanemtnle to form rapidly even at room temper ature The quaternary ammonium salt is acting as a catalyst it increases the reaction rate How7... 

Quaternary ammonium salts catalyze the reaction between an anion and an organic substrate by transfemng the anion from the aqueous phase where it cannot contact the substrate to the organic phase In the example just cited the first step occurs m the... 

Even the tertiary amine competes with ammonia for the alkylating agent The product is a quaternary ammonium salt... 

Because of its high reactivity toward nucleophilic substitution methyl iodide is the alkyl halide most often used to prepare quaternary ammonium salts... 

Quaternary ammonium salts as we have seen are useful m synthetic organic chem istry as phase transfer catalysts In another more direct application quaternary ammo mum hydroxides are used as substrates m an elimination reaction to form alkenes... 

The halide anion of quaternary ammonium iodides may be replaced by hydroxide by treatment with an aqueous slurry of silver oxide Silver iodide precipitates and a solu tion of the quaternary ammonium hydroxide is formed... 

Quaternary ammonium iodide Silver oxide Water Quaternary ammonium hydroxide Silver iodide... 

When quaternary ammonium hydroxides are heated they undergo p elimination to form an aUcene and an amine... 

Quaternary ammonium salts compounds of the type R4N" X find application m a technique called phase transfer catalysis A small amount of a quaternary ammonium salt promotes the transfer of an anion from aqueous solution where it is highly solvated to an organic solvent where it is much less solvated and much more reactive... 

Ammonia can act as a nucleophile toward primary and some secondary alkyl halides to give primary alkylamines Yields tend to be modest because the primary amine IS itself a nucleophile and undergoes alkylation Alkylation of ammonia can lead to a mixture containing a primary amine a secondary amine a tertiary amine and a quaternary ammonium salt... 

Alkylation (Section 22 12) Amines act as nucleophiles toward alkyl halides Pri mary amines yield secondary amines secondary amines yield tertiary amines and tertiary amines yield quaternary ammonium salts... 

Quaternary ammonium hydroxides un dergo elimination on being heated It is an anti elimination of the E2 type The regioselectivity of the Hofmann elimina tion IS opposite to that of the Zaitsev rule and leads to the less highly substi tuted alkene... 

Physostigmme an alkaloid obtained from a West African plant is used in the treatment of glaucoma Treatment of physostigmme with methyl iodide gives a quaternary ammonium salt What IS the structure of this salt" ... 

Quantum (Section 13 1) The energy associated with a photon Quaternary ammonium salt (Section 22 1) Salt of the type R4N X The positively charged ion contains a nitrogen with a total of four organic substituents (any combination of alkyl and aryl groups)... 

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