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- Amine_alkylation abstract "Amine alkylation (amino-de-halogenation) is a type of organic reaction between an alkyl halide and ammonia or an amine. The reaction is called nucleophilic aliphatic substitution (of the halide), and the reaction product is a higher substituted amine. The method is widely used in the laboratory, but is less important industrially, where alkyl halides are not preferred alkylating agents.Alkylation of an amineWhen the amine is a tertiary amine the reaction product is a quaternary ammonium salt in the Menshutkin reaction:Alkylation of a tertiary amineAmines and ammonia are generally sufficiently basic to undergo direct alkylation, often under mild conditions. The reactions are difficult to control because the reaction product (a primary amine or a secondary amine) are often more nucleophilic than the precursor and will thus preferentially react with the alkylating agent. For example, reaction of 1-bromooctane with ammonia yields almost equal amounts of the primary amine and the secondary amine. Therefore, for laboratory purposes, N-alkylation is often limited to the synthesis of tertiary amines. A notable exception is the reactivity of alpha-halo carboxylic acids that do permit synthesis of primary amines with ammonia. Intramolecular reactions of haloamines X-(CH2)n-NH2 give cyclic aziridines, azetidines and pyrrolidines. N-alkylation is a general and useful route to quaternary ammonium salts from tertiary amines, because overalkylation is not possible.Examples of N-alkylation with alkyl halides are the syntheses of benzylaniline, 1-benzylindole, and azetidine. Another example is found in the derivatization of cyclen. Industrially, ethylenediamine is produced by alkylation of ammonia with 1,2-dichloroethane.".
- Amine_alkylation thumbnail Alkylation_of_amine.svg?width=300.
- Amine_alkylation wikiPageID "23902325".
- Amine_alkylation wikiPageLength "5473".
- Amine_alkylation wikiPageOutDegree "33".
- Amine_alkylation wikiPageRevisionID "680400727".
- Amine_alkylation wikiPageWikiLink 1,2-Dichloroethane.
- Amine_alkylation wikiPageWikiLink 1,2-dichloroethane.
- Amine_alkylation wikiPageWikiLink Alkyl_halide.
- Amine_alkylation wikiPageWikiLink Amine.
- Amine_alkylation wikiPageWikiLink Ammonia.
- Amine_alkylation wikiPageWikiLink Arene_substitution_pattern.
- Amine_alkylation wikiPageWikiLink Arene_substitution_patterns.
- Amine_alkylation wikiPageWikiLink Aryl_halide.
- Amine_alkylation wikiPageWikiLink Azetidine.
- Amine_alkylation wikiPageWikiLink Aziridine.
- Amine_alkylation wikiPageWikiLink Base_(chemistry).
- Amine_alkylation wikiPageWikiLink Basicity.
- Amine_alkylation wikiPageWikiLink Buchwald-Hartwig_reaction.
- Amine_alkylation wikiPageWikiLink Buchwald–Hartwig_amination.
- Amine_alkylation wikiPageWikiLink Category:Organic_reactions.
- Amine_alkylation wikiPageWikiLink Cyclen.
- Amine_alkylation wikiPageWikiLink Delépine_reaction.
- Amine_alkylation wikiPageWikiLink Dimethylamine.
- Amine_alkylation wikiPageWikiLink Electron-withdrawing_group.
- Amine_alkylation wikiPageWikiLink Epoxide.
- Amine_alkylation wikiPageWikiLink Ethanolamine.
- Amine_alkylation wikiPageWikiLink Ethylenediamine.
- Amine_alkylation wikiPageWikiLink Gabriel_synthesis.
- Amine_alkylation wikiPageWikiLink Haloalkane.
- Amine_alkylation wikiPageWikiLink Hexamethylenetetramine.
- Amine_alkylation wikiPageWikiLink Hexamine.
- Amine_alkylation wikiPageWikiLink Intramolecular.
- Amine_alkylation wikiPageWikiLink Intramolecular_reaction.
- Amine_alkylation wikiPageWikiLink Menshutkin_reaction.
- Amine_alkylation wikiPageWikiLink Methanol.
- Amine_alkylation wikiPageWikiLink Methylamine.
- Amine_alkylation wikiPageWikiLink Nucleophilic_aliphatic_substitution.
- Amine_alkylation wikiPageWikiLink Nucleophilic_substitution.
- Amine_alkylation wikiPageWikiLink Organic_reaction.
- Amine_alkylation wikiPageWikiLink Polar_effect.
- Amine_alkylation wikiPageWikiLink Pyrrolidine.
- Amine_alkylation wikiPageWikiLink Trimethylamine.
- Amine_alkylation wikiPageWikiLink File:Alkylation_of_amine.svg.
- Amine_alkylation wikiPageWikiLink File:Buchwald_Hartwig_reaction.png.
- Amine_alkylation wikiPageWikiLink File:Formation_of_Quat.PNG.
- Amine_alkylation wikiPageWikiLinkText "Amine alkylation".
- Amine_alkylation wikiPageWikiLinkText "alkylated".
- Amine_alkylation wikiPageWikiLinkText "alkylation".
- Amine_alkylation wikiPageWikiLinkText "amine alkylation".
- Amine_alkylation hasPhotoCollection Amine_alkylation.
- Amine_alkylation wikiPageUsesTemplate Template:Reflist.
- Amine_alkylation subject Category:Organic_reactions.
- Amine_alkylation hypernym Reaction.
- Amine_alkylation type Disease.
- Amine_alkylation type Reaction.
- Amine_alkylation comment "Amine alkylation (amino-de-halogenation) is a type of organic reaction between an alkyl halide and ammonia or an amine. The reaction is called nucleophilic aliphatic substitution (of the halide), and the reaction product is a higher substituted amine.".
- Amine_alkylation label "Amine alkylation".
- Amine_alkylation sameAs m.076v1f2.
- Amine_alkylation sameAs Q4746409.
- Amine_alkylation sameAs Q4746409.
- Amine_alkylation wasDerivedFrom Amine_alkylation?oldid=680400727.
- Amine_alkylation depiction Alkylation_of_amine.svg.
- Amine_alkylation isPrimaryTopicOf Amine_alkylation.