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A molecule containing an amino group, -NH2 , -NHR, or -NR2 , obtained by removing one or more hydrogen atoms from ammonia, with the general formula RNH2 , RNHR, or RNR2 . A primary amine has one R group attached to the N atom, a secondary amine has two R groups attached to the N atom, and a tertiary amine has three R groups attached to the N atom |
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An amine that has one or more alkyl groups attached to the amine nitrogen, such as RNH2 |
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The -NH2 group; if alky1ated, it becomes an alkylamino group -NHR, or a dialkylamino group -NR2 |
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An amine that has one or more aromatic groups attached to the amine nitrogen, such as ArNH2 |
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A derivative of an amine with a positively charged nitrogen atom having four bonds; an amine is protonated by an acid to give an ammonium salt: RNH2 + HA → RN+H3 A- ; a quaternary ammonium salt has a positively charged nitrogen atom bonded to four alkyl (or aryl) groups: R4N+ . Also called aminium salt, or amine salt |
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A compound having the azido group, -N3 |
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of primary amines by alkylation of the potassium salt of phthalimide, followed by displacement of the amine by hydrazine |
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The reduction of an imine or oxime derivative of a ketone or aldehyde to an amine |
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Conversion of a primary carboxylic amide to a primary amine, with one fewer carbon atom, by treatment with bromine in aqueous NaOH, via an isocyanate intermediate. Also called Hofmann reaction |
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Conversion of a carboxylic acid to an amine having one fewer carbon atoms, which proceeds via thermal decomposition of an acyl azide into an isocyanate. Also called Curtius reaction |
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Diazotization of an amine |
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The reaction of a primary aromatic amine with nitrous acid, HNO2 , which forms a diazonium ion, R-N+≡N: and can be used to prepare aryl halides, phenols, and aryl cyanides, or to deaminate the amine |
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Ion of the type R-N+≡N: Aryl diazonium ions are formed by treatment of primary aromatic amines with nitrous acid, HNO2 , which can be used to prepare aryl halides, phenols, and aryl cyanides, or to deaminate the amine |
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An amine with a nitroso group -N=O bonded to the amine nitrogen atom; the reaction of secondary amines with nitrous acid gives secondary nitrosoamines |
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Replacement of the -N≡N group in an arenediazonium salt by a cuprous salt; usually cuprous chloride, bromide, or cyanide |
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The use of an electrophilic diazonium salt in electrophilic aromatic substitution, such as the reaction of an aryl diazonium salt with an arene, which forms a compound of the type ArN=NAr'. The arene must be strongly activated toward electrophilic aromatic substitution; that is, it must bear a powerful electron-releasing substituent such as -OH or -NR2 |
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An amide of a sulfonic acid, which is the nitrogen analogue of a sulfonate ester |
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The reaction of an amine with benzenesulfonyl chloride to form a benzenesulfonamide, in order to determine whether it is a primary, secondary, or tertiary amine |
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Elimination of a quaternary ammonium hydroxide by pyrolysis into an alkene and a tertiary amine, which usually gives the least-substituted alkene (Hofmann product). Also called Hofmann degradation |
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The major product of an elimination reaction that uses a large, bulky base will be the less stable alkene, which has the less substituted double bond. |
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Pyrolysis of a tertiary amine oxide into an alkene and a hydroxylamine |
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An amine that occurs naturally in many plants, fungi and bacteria, and has profound physiological effects on animals, often toxic; the name derives from the word alkaline, since these compounds are weak bases with a bitter taste |
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