Amines sentence example

amines
  • Taking as types hydrogen, hydrochloric acid, water and ammonia, he postulated that all organic compounds were referable to these four forms: the hydrogen type included hydrocarbons, aldehydes and ketones; the hydrochloric acid type, the chlorides, bromides and iodides; the water type, the alcohols, ethers, monobasic acids, acid anhydrides, and the analogous sulphur compounds; and the ammonia type, the amines, acid-amides, and the analogous phosphorus and arsenic compounds.
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  • Stannous chloride and hydrochloric acid reduce the nitroparaffins to 0-alkyl hydroxylamines, amines and some ammonia being simultaneously produced (V.
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  • Carbon bisulphide combines with primary amines to form alkyl dithiocarbamates, which when heated lose sulphuretted hydrogen and leave a residue of a dialkyl thio-urea, CS 2 +2R NH 2 - R NH CSS NH 3 RCS(NHR)2+H2S; or if the aqueous solution of the dithiocarbamate be boiled with mercuric chloride or silver nitrate solution, a mustard oil (q.v.) is formed, R.NH CSS NH3R+HgC12-Hg(R NH CSS)2->2RNCS-}-HgS+H2S.
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  • Wurtz discovered the amines or substituted ammonias, previously predicted by Liebig; A.
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  • An important class of compounds, termed amines (q.v.), results from the condensation of alcohols with ammonia, water being eliminated between the alcoholic hydroxyl group and a hydrogen atom of the ammonia.
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  • Three types of amines are possible and have been prepared: primary, R.
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  • From the primary amines are derived the diazo compounds and azo compounds; closely related are the hydrazines (q.v.).
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  • Secondary amines yield nitrosamines, R 2 N NO, with nitrous acid.
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  • The amines also exhibit striking differences: in the aliphatic series these compounds may be directly formed from the alkyl haloids and ammonia, but in the benzene series this reaction is quite impossible unless the haloid atom be weakened by the presence of other substituents, e.g.
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  • The same difference attends the introduction of the methyl group into many classes of compounds, for example, the paraffins, olefines, acetylenes, aromatic hydrocarbons, alcohols, aldehydes, ketones and esters, while a slightly lower value (157.1) is found in the case of the halogen compounds, nitriles, amines, acids, ethers, sulphides and nitro compounds.
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  • The combination of nitrogen with carbon may result in the formation of nitriles, cyanides, or primary, secondary or tertiary amines.
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  • In the case of the amines he decides in favour of the formulae H2C: NH3 2C NH2 H 3 C. NH CH3 H primary, secondary, tertiary.
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  • These formulae, however, only apply to aliphatic amines; the results obtained in the aromatic series are in accordance with the usual formulae.
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  • On reduction by sodium amalgam in glacial acetic acid solution they yield primary amines.
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  • The acid finds considerable use in organic chemistry, being employed to discriminate between the different types of alcohols and of amines, and also in the production of diazo, azo and diazo-amino compounds.
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  • Dry hydrochloric acid gives ammonia but no nitrogen; with ammonia it gives N:SNH 2 and S :S(NH 2) 2; and with secondary amines it forms thiodiamines, S(NR2)2, nitrogen and ammonia being liberated.
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  • Reduction with acid-reducing agents gives amines.
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  • When reduced by the Sabatier and Senderens' method (Comptes rendus, 1902, 135, p. 225) they are converted into amines, provided the temperature be kept at 150°-200° C., a higher temperature leading to the formation of paraffins and ammonia.
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  • In acid solution, amines are obtained, in alkaline solution, azoxy, azo and hydrazo compounds, and in neutral solution hydroxylamino compounds.
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  • The electrolytic reduction of the aromatic nitro compounds gives rise to substituted hydroxylamines which are immediately transformed into aminophenols or amines.
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  • It combines directly with acetone and with various amines.
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  • It is a colourless solid which melts at 92° C. For silicon derivatives of the amines see Michaelis, Ber., 1896, 29, p. 710; on asymmetric silicon and the resolution of dl-benzyl-ethyl-propyl-silicol see F.
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  • The replacement of one hydrogen atom by one alkyl or aryl group gives rise to primary amines; of two hydrogen atoms by two groups, to secondary amines; of three hydrogen atoms by three groups, to tertiary amines.
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  • The tertiary amines possess the power of combining with one molecular proportion of an alkyl iodide to form quaternary ammonium salts.
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  • Aliphatic amines.
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  • Many methods have been devised for the preparation of the amines, the first amine having been isolated in 1849 by A.
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  • By the action of ammonia on the alkyl iodides a complex mixture of primary, secondary and tertiary amines, along with a quaternary ammonium salt, is obtained, the separation of which is difficult.
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  • Hofmann is as follows: the mixture is distilled with caustic potash, when the primary, secondary and tertiary amines distil over, and the quaternary ammonium salt remains behind unaffected.
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  • The aqueous solution of the amines is now shaken up with diethyl oxalate, when the primary amine forms a crystalline dialkyl oxamide and the secondary amine an insoluble liquid, which is an ethyl dialkyl oxamate, the tertiary amine not reacting: (C02C2H5)2+ 2NH 2 R = (CO�NHR) 2 -{- 2C 2 H S OH; (CO 2 C 2 H 5) 2 -}- NHR 2 = C 2 H S O 2 C�Conr 2 -1-C 2 H S Oh.
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  • The primary, secondary and tertiary amines may be readily distinguished by their behaviour with various reagents.
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  • Primary amines when heated with alcoholic potash and chloroform yield isonitriles, which are readily detected by their offensive smell.
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  • The secondary and tertiary amines do not give this reaction.
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  • With nitrous acid, the primary amines yield alcohols, the secondary amines yield nitrosamines and the tertiary amines do not react: R�NH 2 +0NOH= R�OH+N2+H20; R2NH+ [[Onoh= R 2 N�No H]] 2 0.
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  • With benzene sulphochloride in the presence of alkali, the primary amines yield compounds of the type C 6 H 5 S0 2 NHR, soluble in alkalies, whilst the secondary amines yield compounds of the type C 6 H 5 S0 2 NR 2, insoluble in alkalies (0.
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  • Primary amines heated with carbon bisulphide in alcoholic solution are converted into mustard oils, when the dithiocarbamate first produced is heated with a solution of mercuric chloride.
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  • Aromatic Amines.-The aromatic amines in some respects resemble the aliphatic amines, since they form salts with acids, and double salts with platinum chloride, and they also distil without decomposition.
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  • The primary aromatic amines may be prepared by the reduction of the nitro-hydrocarbons, the reducing agents used being either alcoholic-ammonium sulphide (N.
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  • At a temperature of about 300-400° C. the alkyl chloride formed in this reaction attacks the benzene nucleus and replaces hydrogen by an alkyl group or groups, forming primary amines homologous with the original amine; thus methylaniline hydrochloride is converted into paraand ortho-toluidine hydrochloride, and trimethyl phenyl ammonium iodide is converted into mesidine hydriodide.
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  • It is to be noted that only traces of the aromatic amines are produced by heating the halogen substituted benzenes with ammonia, unless the amino group be situated in the side chain, as in the case of benzylamine.
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  • The primary amines are colourless liquids or crystalline solids, which are insoluble in water, but readily soluble in the common organic solvents.
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  • When heated with alkyl or aryl iodides, they are converted into secondary and tertiary amines.
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  • The mixed secondary amines are prepared by the action of alkyl iodides on the primary amines, or by heating salts of the primary amine with alcohols under pressure.
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  • The mixed secondary amines have basic properties, but the purely aromatic secondary amines are only very feeble bases.
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  • The secondary amines do not give the isonitrile reaction.
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  • The tertiary amines may also be of two types, the purely aromatic and the mixed type.
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  • The mixed tertiary amines are produced by the action of alkyl halides on the primary amines.
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  • The simplest aromatic monamine is aniline, and the simplest mixed amines are monoand di-methyl aniline.
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  • The aromatic amine resembling the aliphatic amines is benzylamine, C 6 H 5 �CH 2 �NH 2, which may be prepared by reducing benzonitrile in alcoholic solution by means of zinc and acetic acid (0.
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  • Diphenylamine, (C6H5)2NH, is the simplest representative of the true aromatic secondary amines.
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  • Substituted oxamides are produced by the action of primary amines on ethyl oxalate.
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  • Auric chloride combines with the hydrochlorides of many organic bases - amines, alkaloids, &c. - to form characteristic compounds.
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  • When reduced by sodium in boiling amyl alcohol solution it forms alicyclic tetrahydro-0naphthylamine, which has most of the properties of the aliphatic amines; it is strongly alkaline in reaction, has an ammoniacal odour and cannot be diazotized.
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  • SAFRANINE, in chemistry, the azonium compounds of symmetrical diamino-phenazine and containing the ring system annexed: / N / or X N .% CI R C1 R They are obtained by the joint oxidation' of one molecule of a paradiamine with two molecules of a primary amine; by the condensation of para-aminoazo compounds with primary amines (0.
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  • Other constituents are cholesterol (0.461.32%), traces of calcium, magnesium, sodium, chlorine and bromine, and various aliphatic amines which are really secondary products, being formed by the decomposition of the cellular tissue.
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  • 3, p. 319.) Ammonia finds a wide application in organic chemistry as a synthetic reagent; it reacts with alkyl iodides to form amines, with esters to form acid amides, with halogen fatty acids to form amino-acids; while it also combines with isocyanic esters to form alkyl ureas and with the mustard oils to form alkyl thioureas.
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  • Eltekow, Ber., 1878, 11, p. 414); by the action of metals on the halogen compounds Cn.H 20 Br 2 i by boiling the aqueous solution of nitrites of the primary amines (V.
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  • Paraquinones also combine with ammonia and with amines yielding amino-derivatives and hydroquinones.
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  • They behave in most respects as unsaturated compounds; they combine with hydrogen to form amines; with water to form acidamides; with sulphuretted hydrogen to form thio-amides; with alcohols, in the presence of acids, to form imido-ethers R C(:NH) OR'; with ammonia and primary amines to form amidines R C(:NH) NH 2 i and with hydroxylamine to form amidoximes, R C(:NOH) NH 2.
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  • They boil at temperatures somewhat lower than those of the corresponding nitriles; and are stable towards alkalis, but in the presence of mineral acids they readily hydrolyse, forming primary amines and formic acid: RNC+2H 2 O = RNH2+H2C02.
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  • By oxidizing agents they are converted into azoxy compounds, and by reducing agents into hydrazo compounds or amines.
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  • Alkylated amino-azo-benzenes are also known, and are formed by the coupling of diazonium salts with alkylated amines, provided they contain a free para.
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  • Diazo-Amines.-The diazo-amines, R N: N NHR I, are obtained by the action of primary amines on diazonium salts; by the action of nitrous acid on a free primary amine, an isodiazohydroxide being formed as an intermediate product which then condenses with the amine; and by the action of nitrosamines on primary amines.
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  • When reduced (in acid solution) they yield amines; distillation with reduced iron gives azo compounds, and warming with ammonium sulphide gives hydrazo compounds.
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  • The -y-diketones are characterized by the readiness with which they yield furfurane, pyrrol and thiophene derivatives, the furfurane derivatives being formed by heating the ketones with a dehydrating agent, the thiophenes, by heating with phosphorus pentasulphide, and the pyrrols by the action of alcoholic ammonia or amines.
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  • The diazonium salts are also formed by the action of zinc-dust and acids on the nitrates of primary amines (R.
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  • Bamberger (Ber., 18 94, 27, p. 9 1 4) obtained the diazoic acids, R NH NO 2, substances which he had previously prepared by similarly oxidizing the diazonium salts, by dehydrating the nitrates of primary amines with acetic anhydride, and by the action of nitric anhydride on the primary amines.
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  • NHR, may be prepared by the action of the primary and secondary amines on the diazonium salts, or by the action of nitrous acid on the free primary amine.
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  • The esters of the aliphatic amino acids may be diazotized in a manner similar to the primary aromatic amines, a fact discovered by T.
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  • NH 2, which may be considered as derived from the acid-amides by replacement of oxygen by the divalent imino (= NH) group. They may be prepared by the action of ammonia or amines on imide chorides, or on thiamides (0.
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  • Bernthsen); by the action of ammonium chloride or hydrochlorides of amines on nitriles; by condensing amines and amides in presence of phosphorus trichloride; by the action of hydrochloric acid on acid-amides (0.
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  • Urea chlorides are formed by the action of carbonyl chloride on ammonium chloride (at 400° C.), or on salts of primary amines.
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  • Alkyl ureas are formed by the action of primary or secondary amines on isocyanic acid or its esters: [[Conh+Nh2r= R Nhc0nh]] 2 i [[Conr+Nhr 2 =Nr 2 Co Nhr]]; by the action of carbonyl chloride on amines: COC12+2NHR2=C0(NR2)2+2HC1; and in the hydrolysis of many ureides.
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  • Hydrolysis by alkalis decomposes them into carbon dioxide, amines and ammonia.
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  • The dialkyl thioureas when digested with mercuric oxide and amines give guanidines.
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  • Amines >>
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  • Amidotetrazotic acid yields addition compounds with amines, and by the further action of nitrous acid yields a very explosive derivative, diazotetrazol, CN 3.
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  • It combines with aromatic amines to form azocompounds, with arylhydroxylamines to form azoxy compounds, and with hydroxylamine it gives isodiazobenzene.
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  • By the condensation of ortho-aminophenols with phosgene or thiophosgene, oxy and thio-derivatives are obtained, the (OH) and (SH) groups being situated in the t t position, and these compounds on treatment with amines yield amino derivatives.
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  • They are characterized by their additive reactions: combining with water to form acids, with alcohols to form esters, and with primary amines to form amides.
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  • It melts at 64° C. and boils at 250-252° C. The aminopyridines are readily soluble in water, and resemble the aliphatic amines in their general chemical properties.
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  • Just as the amines are derived from ammonia, so from phosphine are derived the primary, secondary and tertiary organic phosphines by the exchange of hydrogen for alkyl groups, and corresponding to the phosphonium salts there exists a series of organic phosphonium bases.
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  • With methyl and ethyl alcohols it forms secondary amines (Vidal, Comptes rendus, 1891, 112, p. 950; 1892, 115, p. 123).
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  • The reaction is a perfectly general one, for the aniline may be replaced by other aromatic amines and the aldehyde by other aldehydes, and so a large number of quinoline homologues may be prepared in this way.
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  • Furthermore, he exhibited a comparison between these three types of alcohols and the amines.
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  • Primary alcohols are obtained by decomposing their sulphuric acid esters (from sulphuric acid and the olefines) with boiling water; by the action of nitrous acid on primary amines; or by the reduction of aldehydes, acid chlorides or acid anhydrides.
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  • Aniline combines directly with alkyl iodides to form secondary and tertiary amines; boiled with carbon disulphide it gives sulphocarbanilide (diphenyl thio-urea), CS(NHC 6 H 5) 2, which may be decomposed into phenyl mustard-oil, C 6 H 5 CNS, and triphenyl guanidine, C 6 H 5 N: C(NHC6H5)2.
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  • aliphatic primary amines are stronger bases than ammonia.
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  • These acids can be further refined to make fatty alcohols, metallic soaps, fatty amines, fatty acid esters and fatty amides.
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  • Ammonia and its aqueous solution form complexes called amines with many salts.
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  • amines formed together with their salts.
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  • Components of cooked meat that have been suggested to cause this include heterocyclic amines, polycyclic aromatic hydrocarbons, nitrogenous residues and iron.
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  • Alternatively, the problem might be caused by compounds called heterocyclic amines, carcinogenic compounds created in the cooking process.
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  • All aliphatic primary amines are stronger bases than ammonia.
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  • Physical properties of amines (structure, hydrogen bonding, basicity ).
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  • heterocyclic amines, carcinogenic compounds created in the cooking process.
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  • Synthesis of acidic aluminosilicate mesoporous molecular sieves using primary amines, Chem.
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  • pressor amines in MAOI regimens: a review.
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  • reactions of amines as nucleophiles.
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  • By the action of bromine and alcoholic potash on the amides,, they are converted into amines containing one carbon atom less than the original amide, a reaction which possesses great.
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  • It is worthy of note that phosphorus and arsenic bases analogous to the amines are known (see Phosphorus and Arsenic).
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  • By condensation of aldehydes with pyruvic acid and naphthylamines, the a-alkyl-naphthoquinoline-y-carboxylic acids are produced; the same reaction takes place with the aromatic amines generally (0.
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  • When reduced by the Sabatier and Senderens' method (Comptes rendus, 1902, 135, p. 225) they are converted into amines, provided the temperature be kept at 150°-200° C., a higher temperature leading to the formation of paraffins and ammonia.
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  • Sandmeyer, Ber., 1887, 20, p. 1494) by the action of copper powder on the double salt formed by the addition of potassium mercuric nitrite to diazonium nitrites; and by the oxidation of primary aromatic amines (E.
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  • It is a colourless solid which melts at 92° C. For silicon derivatives of the amines see Michaelis, Ber., 1896, 29, p. 710; on asymmetric silicon and the resolution of dl-benzyl-ethyl-propyl-silicol see F.
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  • The primary amines may also be prepared by heating the alkyl iodides with ammonia (A.
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  • CON 3 --> R�NH�CO 2 C 2 H 5 - R.NH2 azide urethane The secondary amines are prepared, together with the primary and tertiary, by the action of ammonia on the alkyl iodides (see below), or by the hydrolysis of para-nitroso derivatives ` of tertiary aromatic amines, such as para-nitrosodimethylaniline, thus: NO�C 6 H 4 �N(CH 3) 2 � H 2 O = NO�C 6 H 4.
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  • The aqueous solution of the amines is now shaken up with diethyl oxalate, when the primary amine forms a crystalline dialkyl oxamide and the secondary amine an insoluble liquid, which is an ethyl dialkyl oxamate, the tertiary amine not reacting: (C02C2H5)2+ 2NH 2 R = (CO�NHR) 2 -{- 2C 2 H S OH; (CO 2 C 2 H 5) 2 -}- NHR 2 = C 2 H S O 2 C�Conr 2 -1-C 2 H S Oh.
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  • With nitrous acid, the primary amines yield alcohols, the secondary amines yield nitrosamines and the tertiary amines do not react: R�NH 2 +0NOH= R�OH+N2+H20; R2NH+ [[Onoh= R 2 N�No H]] 2 0.
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  • At a temperature of about 300-400° C. the alkyl chloride formed in this reaction attacks the benzene nucleus and replaces hydrogen by an alkyl group or groups, forming primary amines homologous with the original amine; thus methylaniline hydrochloride is converted into paraand ortho-toluidine hydrochloride, and trimethyl phenyl ammonium iodide is converted into mesidine hydriodide.
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  • The aromatic amine resembling the aliphatic amines is benzylamine, C 6 H 5 �CH 2 �NH 2, which may be prepared by reducing benzonitrile in alcoholic solution by means of zinc and acetic acid (0.
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  • His perception of the analogy between it and ammonia led to his famous work on the amines and ammonium bases and the allied organic phosphorus compounds, while his researches on rosaniline, which he first prepared in 1858, formed the first of a series of investigations on colouring matters which only ended with quinoline red in 1887.
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  • Those of the former type are obtained by condensing a-bromketones with primary amines (A.
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  • They may be prepared by heating the alkyl iodides with potassium cyanide; by heating sulphuric acid esters with potassium cyanide; by distilling the acid-amides with phosphorus pentoxide; and by distilling amines (containing more than five atoms of carbon) with bromine and potash (A.
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  • In addition to these methods, the nitriles of the aromatic series may be prepared by distilling the aromatic acids with potassium sulphocyanide: C 6 H 5 CO 2 H -{- [[Kcns = Hcns -}- C6h5c02k, C 6 H 5 Co 2 H -}- Hcns = C 6 H 5 Cn]] -fH 2 S + C02; from the primary aromatic amines by converting them into diazonium salts, which are then decomposed by boiling with potassium cyanide and copper sulphate; by fusing the potassium salts of the sulphonic acids with potassium cyanide; by leading cyanogen gas into a boiling hydrocarbon in the presence of aluminium chloride (A.
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  • Wallach, Ber., 1882, 15, p. 208); and by the action of ammonia or amines on imino-ethers (A.
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  • Urea chlorides are formed by the action of carbonyl chloride on ammonium chloride (at 400° C.), or on salts of primary amines.
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  • The alkyl derivatives of thiourea are obtained by the action of ammonia and of primary and secondary amines on the mustard oils (A.
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  • It melts at 64° C. and boils at 250-252° C. The aminopyridines are readily soluble in water, and resemble the aliphatic amines in their general chemical properties.
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  • If, however, one of the para positions in the hydrazo compound is substituted, then either diphenyl derivatives or azo compounds are formed, or what is known as the semidine change takes place (P. Jacobson, Berichte, 1892, 2 5, p. 99 2; 1893, 26, p. 681; 1896, 29, p. 2680; Annalen, 1895, 287, p. 97; 1898, 3 0 3, p. 290) A para mono substituted hydrazo compound in the presence of a hydrochloric acid solution of stannous chloride gives either a para diphenyl derivative (the substituent group being eliminated), an ortho-semidine, a para-semidine, or a diphenyl base, whilst a decomposition with the formation of amines may also take place.
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  • This page summarizes the reactions of amines as nucleophiles.
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  • The secondary amines may be of two types-namely,the purely aromatic amines, and the mixed secondary amines, which contain an aromatic residue and an alkyl group. The purely aromatic amines result upon heating the primary amines with their hydrochlorides, and, in some cases, by heating a phenol with a primary amine and anhydrous zinc chloride.
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  • Mixed aromatic-aliphatic amines, both secondary and tertiary, are also more strongly basic than the pure aromatic amines, and less basic than the true aliphatic compounds; e.g.
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  • AMINES, in chemistry, derivatives of ammonia in which one or more of the hydrogen atoms are replaced by alkyl or aryl groups.
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  • On the other hand, they are much weaker bases than the aliphatic amines, their salts undergoing hydrolytic dissociation in aqueous solution.
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