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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.
Amine
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An amine that has one or more alkyl groups attached to the amine nitrogen, such as RNH2
Alkylamine
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The -NH2 group; if alky1ated, it becomes an alkylamino group -NHR, or a dialkylamino group -NR2
Amino group
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An amine that has one or more aromatic groups attached to the amine nitrogen, such as ArNH2
Aryl amine
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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+
Ammonium salt
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A compound having the azido group, -N3
Azide
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Synthesis of primary amines by alkylation of the potassium salt of phthalimide, followed by displacement of the amine by hydrazine
Gabriel amine synthesis
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The reduction of an imine or oxime derivative of a ketone or aldehyde to an amine.
Reductive amination
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A compound with a carbon-nitrogen double bond, R2C=NR', formed by the reaction of a ketone or aldehyde with a primary amine; a substituted imine is often called a Schiff base.
Imine
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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
Hoffman rearrangement
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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
Curtius rearrangement
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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
Diazotization of an 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
Diazonium ion
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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.
Nitrosoamine (N-nitrosoamine)
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Replacement of the -N≡N group in an arenediazonium salt by a cuprous salt; usually cuprous chloride, bromide, or cyanide
Sandmeyer reaction
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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 .
Diazo coupling
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An amide of a sulfonic acid, which is the nitrogen analogue of a sulfonate ester.
Sulfonamide
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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.
Hinsberg test
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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)
Hofmann elimination (aka Hofmann degradation)
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The major product of an elimination reaction that uses a bulky, strong base will be the less stable alkene, which has the less substituted double bond.
Hofmann rule
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Pyrolysis of a tertiary amine oxide into an alkene and a hydroxylamine.
Cope elimination
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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
Alkaloid
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